Name: 7400-08-0|p-Hydroxy-Cinnamic Acid|98%
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SKU: A568414
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1
[ 67-56-1 ]
[ 7400-08-0 ]
[ 3943-97-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sulfuric acid for 24h; Reflux;	General procedure for the synthesis of compounds 9-12 and 21-29 General procedure: After dissolving the carboxylic acid in the alcohol, three drops of H2SO4 95% were added to the solution and the mixture was refluxed for 24 h. The solvent was evaporated under reduced pressure and water was added to the crude mixture. The pH of the aqueous layer was adjusted to 7 adding drops of a saturated solution of NaHCO3 and brine was added in the mixture. The aqueous layer was extracted three times with ethyl acetate; the organic layer was dried over Na2SO4 and the solvent was evaporated under reduced pressure yielding the final compound. Further purification step was made when it was necessary.
99%	With sulfuric acid for 7h; Heating;
99%	With sulfuric acid for 24h; Reflux;

99%	With sulfuric acid for 21h; Reflux;	15 (E)-Methyl 3-(4-hydroxyphenyl)acrylate (E)-Methyl 3-(4-hydroxyphenyl)acrylate (0403) (0404) p-Coumaric acid (3.0 g, 18.3 mmol) was suspended in MeOH (12 mL) and treated with 3 drops of conc. H2SO4. The mixture was refluxed for 21 h. The resulting clear solution was cooled to rt and concentrated under vacuum to yield a white solid that was dissolved in EtOAc and successively washed with sat. NaHCO3 solution (3×) and brine (3×). The organic layer was dried over anhydrous MgSO4 and evaporated to dryness under vacuum to afford 3.22 g (18.1 mmol, 99% yield) of a white solid identified by NMR as (E)-methyl 3-(4-hydroxyphenyl)acrylate. (0405) 1H NMR (400 MHz, CDCl3) δ 7.64 (d, J=16.0 Hz, 1H), 7.43 (ddd, J=8.8, 2.8, 2.0 Hz, 2H), 6.86 (ddd, J=8.8, 2.8, 2.0 Hz, 2H), 6.30 (d, J=16.0 Hz, 1H), 5.47 (br s, 1H), 3.80 (s, 3H).
98%	Heating / reflux;	27.27a Step 27a. (E)-Methyl 3-(4-hydroxyphenyl)acrylate (Compound 0501-66) A mixture of 4-hydroxycinnamic acid (8.2 g, 50 mmol) and a drop of H2SO4 in methanol (30 mL) was heated to reflux overnight. Then the solvent was evaporated, the residue was dissolved in ethyl acetate, washed with saturated NaHCO3 solution twice, brine, dried over MgSO4, concentrated to give the title compound 0501-66 as white solid (8.7 g, 98%): LCMS: 179 [M+1]+.
98%	With sulfuric acid Heating / reflux;	27.a Example 27Preparation of (E)-3-(4-(2-(4-(3-chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-yloxy)ethoxy)phenyl)-N-hydroxyacrylamide (Compound 66)Step 27a. (E)-Methyl 3-(4-hydroxyphenyl)acrylate (Compound 0501-66); A mixture of 4-hydroxycinnamic acid (8.2 g, 50 mmol) and a drop of H2SO4 in methanol (30 mL) was heated to reflux overnight. Then the solvent was evaporated, the residue was dissolved in ethyl acetate, washed with saturated NaHCO3 solution twice, brine, dried over MgSO4, concentrated to give the title compound 0501-66 as white solid (8.7 g, 98%): LCMS: 179 [M+1]+.
97%	With Dowex 50 W (8200 4) Heating;
97%	With sulfuric acid for 12h; Reflux; Inert atmosphere;
96%	With sulfuric acid for 16h; Heating;
95%	With sulfuric acid for 24h; Molecular sieve; Reflux;
95%	With sulfuric acid for 24h; Molecular sieve;
95%	With acetyl chloride In methanol at 20℃; Inert atmosphere;	Preparation of methyl 4-hydroxycinnamate To a solution of anhydrous methanol (50 mL) in round bottom flask under N2 was added acetyl chloride (0.5 mL) followed by a solution of 4-hydroxycinnamic acid (1 g) in anhydrous methanol (10 mL). The mixture was stirred overnight at room temperature, added NaCl solution (20%, 100 mL) then extracted twice with ethyl acetate (150 mL). The organic layers were combined and washed with NaCl solution (20%, 50 mL), dried over MgSO2, then evaporated under reduced pressure. The product was purified by vacuum column chromatography on silica gel to give the title compound as white solid (1.04 g, yield 95%). 1H- and 13C-NMR spectrum were in good agreement with previously reported data[45].
95%	With sulfuric acid for 12h; Reflux;
94%	With sulfuric acid for 0.166667h; Irradiation;
93%	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane for 0.5h;
92%	With toluene-4-sulfonic acid for 24h; Reflux;
92%	With thionyl chloride
90%	With sulfuric acid for 24h; Heating;
89%	for 90h; Reflux; Inert atmosphere;	12 4.12. Methyl (E)-p-coumarate (24) To a solution of p-coumaric acid 22 (3.0 g, 18.3 mmol) in MeOH (40 mL) was added Dowex 50W-X8 (2.4 g) at room temperature and the resulting mixture was refluxed for 90 h. After the Dowex 50W-X8 was filtered, the solvent was removed under reduced pressure and the residue was purified by flash column chromatography (30% AcOEt in hexane) to give a methyl ester with trace impurities. Recrystallization from CHCl3 gave 24 (2.91 g, 89%) as a white solid in a pure form. Mp: 130-132 °C; IR (KBr) 3384, 2952, 1689, 1634, 1602, 1517, 1435, 1284, 1200, 986, 834 cm-1; 1H NMR (600 MHz, CDCl3) δ 3.80 (s, 3H), 5.33 (s, 1H; OH), 6.30 (d, J=16.0 Hz, 1H), 6.85 (d, J=8.5 Hz, 2H), 7.43 (d, J=8.5 Hz, 2H), 7.64 (d, J=16.0 Hz, 1H); 13C NMR (150 MHz, CDCl3) δ 51.7, 115.1, 115.9, 127.1, 130.0, 144.8, 157.8, 168.1; HRMS (FAB) calcd for C10H11O3 [M+H]+ 179.0708, found 179.0700.
88%	at 20℃; for 36h; Reflux;	1.7 (Example 1-7) Synthesis of intermediate 10 for glucose derivative () 3-(4-Hydroxyphenyl)methylacrylate (10) A mixed solution (amixture) of cinnamic acid (5 g, 30.48 mmol) was refluxed for 1.5 days in the presence of dry MeOH (300 mL) and concentrated (conc.) H2SO4 (1 drop). The solution was cooled to room temperature (r.t.) and then evaporated with 30% ammonia water under reduced pressure and neutralized. Finally, the solution was evaporated with EtOH, to thereby obtain a completely dried product. The dried residue was subj ected to silica gel column chromatography, to thereby obtain a colorless needle-like product 10 (4.8 g, 88%) from a fraction eluted with AcOEt-n-hexane (1:4, v/v). Melting point (m.p.) 122-123°C. Rf=0.23 (AcOEt:n-hexane, 1:8, v/v). IR (KBr) cm-1; 1600 (C=C), 1695 (C=O), 3380 (OH). 1H NMR (CDCl3, 300 MHz): δ 3.81 (s, 3H, O-Me), 5.92 [s, 1H, Ar-OH (exchangeable with D2O)], 6.32 (d, J=15.9 Hz, 1H, Ar-CH=CH-), 6.86 (d, 2H, J=8.4 Hz, Ar-H), 7.42 (d, 2H, J=8.4 Hz, Ar-H), 7.67 (d, J=15.9 Hz, 1H, Ar-CH=CH-).
87.98%	With sulfuric acid Reflux;	4.2. General Procedure for Preparation of Compounds 1-8 General procedure: p-Coumaric acid (0.1 g; 0.61 mmol) in alcohol (20 mL) was dissolved in the presence of H2SO4(0.2 mL) and refluxed for complete reaction (5-27 h), being observed using single spot thin-layerchromatography (TLC) [71], as published by Lopes et al. [44].
87%	With sulfuric acid for 24h; Reflux;	30 Example 30 (E) Synthesis of 3-(4-Hydroxyphenyl) Methyl Acrylate Add 4-hydroxycinnamic acid (1mmol, 164mg)Dissolved in anhydrous methanol (5mL),Add sulfuric acid (1 drop) under stirring at room temperature,The reaction was heated to reflux for 24 hours.Cool down the mixture,And the solvent was removed in vacuo.The residue was dissolved in ethyl acetate (30 mL),And use saturated sodium bicarbonate aqueous solution (20mL)Wash with saturated aqueous NaCl solution (2×20 mL).After filtering, dry with anhydrous Na2SO4,After the filtrate is concentrated,Separation and purification by column chromatography,The eluent is EtOAc:petroleum ether=1:5,A white solid compound is obtained,The yield was 87%.
85%	With thionyl chloride at 0℃; Reflux; Inert atmosphere;	5.2. General procedure for preparation of esters General procedure: Thionyl chloride (1.16 g, 1.5 equiv) was added drop-wise to a solution of acid (1.0 g, 1.0 equiv) in the corresponding alcohol (15 ml) at 0&d eg;C. The solution was refluxed under a nitrogen atmosphere until all starting material was consumed (TLC monitoring). Then the solvent was removed under vacuo and the residue was purified by silica gel column chromatography eluting with ethyl acetate/n-hexane to afford the corresponding carboxylic esters.
82%	With sulfuric acid for 5.5h; Heating;
82%	With sulfuric acid at 80℃; for 0.25h; Microwave irradiation;	4.1.3. General Procedure for the Synthesis of Compounds 14-17 General procedure: In a 30 mL glass pressure microwave tube, equipped with a magnetic stirrer bar, a fewdrops of concentrated sulphuric acid were added to a solution of hydroxycinnamic acid(p-coumaric acid or caffeic acid or ferulic acid) (1 eq) in methanol (for 14-16) or ethanol(for 17) (10 mL). The mixture was subjected to microwave irradiation (power: 150 W;temperature: 80 C for 14-16 and 98 C for 17) for 15 min, basified with aqueous sodiumbicarbonate (5% solution), and extracted with dichloromethane (3 5 mL). The collectedorganic phases were dried over anhydrous sodium sulphate and evaporated to dryness togive the pure ester. (E)-Methyl 3-(4-hydroxyphenyl)acrylate 14: white solid; 82%; mp 125-127 C ([58] 132-134 C); 1H-NMR 3.79 (s, 3H), 5.37 (bs, 1H), 6.28 (d, J = 16.0 Hz, 1H), 6.85 (m, Ar, 2H), 7.42(m, Ar, 2H), 7.63 (d, J = 16.0, 1H); 13C-NMR 51.75, 114.52, 115.91, 125.98, 129.89, 144.79,158.12, 167.65. Anal. Calcd. for C10H10O3 C, 67.41; H, 5.66; Found: C, 67.53; H, 5.56.
79%	With sulfuric acid at 60℃; for 72h;
78%	With sulfuric acid at 45℃; for 2h;
78%	With sulfuric acid for 24h; Heating;
77.8%	With sulfuric acid at 80℃; for 5h;	Prerjaration of reagent KR-28: Methyl (E)-3-(4-hydroxyrjhenyl)rjrorj-2-enoate A solution of the commercially available trans-4-hydroxycinnamic acid, 16, (5 g, 30.5 mmol) in MeOH (30 mL) was added H2504 (3 mL), then the mixture was stirred at 80 00 for 5 h. The resulting mixture was cooled to room temperature and concentrated under vacuo. The mixture was quenched into water, extracted with EA, dried with anhydrous Na2504, concentrated to givethe product KR-28 (4.2 g, 77.8%) as a pale yellow solid. ESI-MS (Mi-i): 179.1 calc. for 010H1003: 178.0.
75%	With sulfuric acid for 2h; Reflux;	Synthesis of (E)-methyl 3-(4-hydroxyphenyl)acrylate (13): A 5 gof trans-4-hydroxy cinnamic acid (12) (30.49 mmol, 1 equiv) was dissolved in 20 mL of methanol. A 0.33 mL of conc. H2SO4 (6.10 mmol, 0.2 equiv) was added. This reaction mixture was refluxed for 2 hr. Methanol was evaporated and the reaction mixture was washed with aq. NaHCO3 solution. Further it was extracted in ethyl acetate and concentrated to get desired compound. Light pale yellow liquid, Yield: 75%, Rf: 0.5 (2:8 EtOAc: hexane), IR (cm-1): 1595 (C=C), 1680 (C=O), 2357(C-H), 3281(O-H). 1H NMR (400 MHz, CDCl3): δ 3.71(s, 3H,CH3); 6.31 (d, 1H, J = 16 Hz, CH=CH); 6.79 (m, 2H); 7.44-7.47(m, 2H); 7.55 (d, 1H, J = 16 Hz, CH=CH); 9.85 (s, 1H, OH); 13C NMR (CDCl3): δ 50.00, 113.69, 115.66, 124.91, 129.85, 144.53, 159.76,166.87; MS-ESI (m/z):179.59 (M+1).
74.1%	With boron trifluoride diethyl etherate at 70℃; for 2h;	1 Boron trifluoride etherate (0.067 mol) is added to a solution of coumaric acid (0.034 mol) in methanol (50 ml) in a 250 ml round bottom flask and the mixture stirred at 70° C. for 2 hours and evaporated to dryness under reduced vacuum. The residual solid is taken up in CH2Cl2, washed with aqueous NaHCO3, dried over MgSO4 and filtered to provide, after evaporation of the CH2Cl2, the desired product as a pale yellow solid in 74.1% yield.
74%	With acetyl chloride at 20℃;
63%	With sulfuric acid Heating;
58%	With sulfuric acid for 2h; Reflux;
57%	With sulfuric acid for 3h;	2.3. Synthesis of the esters General procedure: The ester derivatives (b-f) were synthesized following classicFischer esterification [18] using 1 mmol of the corresponding acid,0.1 mL of concentrated sulfuric acid and the corresponding alcohol assolvent. The reaction proceeded for 3 h or until no more acid was observedin TLC. The reaction mixture was neutralized with aqueousNaHCO3 saturated solution, and the solvent excess was evaporatedunder reduced pressure. The residue was taken up in 10 mL ethylacetate and washed with 3x10 mL of saturated NaHCO3 solution and10 mL of water. The organic layer was dried with anhydrous Na2SO4.The desired compounds were further purified in a silica gel columnchromatography, using hexane:ethyl acetate as eluent.Methyl p-coumarate (1b). White solid (m.p. 134-136 °C); 57% yield.1H NMR (CDCl3) δ 7.65 (d, J = 16.0 Hz, 1H), 7.42 (d, J = 8.6 Hz, 2H),6.86 (d, J = 8.6 Hz, 2H), 6.30 (d, J = 16.0 Hz, 1H), 6.11 (s, 1H), 3.81(s, 3H).
56%	With sulfuric acid Reflux;	2.3. General procedure for the synthesis of the esters General procedure: The ester derivatives (p-coumarates 1a-c and cinnamates 2a-c) weresynthesized following classic Fischer esterification. In a flask, 1 mmol ofthe corresponding acid (1 or cinnamic acid 2) and 0.1 mL of concentratedsulfuric acid were added to an excess (10 mL) of correspondingalcohol (methanol, ethanol or isopropanol) as solvent. Thereaction mixture was stirred under reflux for 3-24 hours until no morestarting acid was present (monitored by thin layer chromatography,TLC). The acid was neutralized with saturated sodium bicarbonate solution,and the excess of alcohol was evaporated under reduced pressure.The residue was taken up in 15 mL ethyl acetate and washed threetimes with 15 mL saturated sodium bicarbonate solution and dried overanhydrous sodium sulfate. The solvent was removed and the crudeproduct was purified through open silica gel column chromatographyusing hexane:ethyl acetate as eluent. The yields are given after chromatographicpurification.
54.4%	With sulfuric acid Reflux;	3.1 General procedure for the synthesis of compounds General procedure: A mixture of organic acid (0.5 g) and methanol (100 ml) was heated under reflux in presence of sulphuric acid (0.8 ml) until the completion of the reaction which was checked by single spot TLC. Then, methanol was removed under reduced pressure a half and the solution was diluted with 20 ml of water. The product was extracted with ethyl acetate (30 ml). The organic phase was neutralized successively with NaHCO3 5%and water, dried over anhydrous Na2SO4, and filtered. The ethyl acetate phase was separated, which on evaporation yielded the ester derivatives
17%
	With sulfuric acid at 75 - 80℃; unter Druck;
	With sulfuric acid
	With hydrogenchloride for 5h;
	With hydrogenchloride for 6h; Heating;
	With Dowex 50W-8X cation-exhange resin for 3h;
	With Dowex 50 W x 8200-400 Heating;
	With sulfuric acid at 90℃; for 16h;
	With hydrogenchloride Heating;
	With thionyl chloride at 23℃; for 16h;
	With toluene-4-sulfonic acid for 5h; Heating;
	With sulfuric acid for 12h; Heating;
	at 20℃;
	With boron trichloride at 55℃; for 0.0833333h;
	With sulfuric acid for 16h; Heating;
	Stage #1: methanol With thionyl chloride at 0℃; for 0.5h; Stage #2: p-Coumaric Acid for 1.5h; Heating / reflux;	106 Thionyl chloride (1.75 mL) was dropwise added under stirring to methanol at 0°C. After 30 minutes 4-hydroxycinnamic acid (3.29 g) was added and the mixture was refluxed for 1.5 h. The solvent was evaporated in vacuo and the residue was crystalized from diisopropyl ether and hexane to give Compound (106) (2.41 g) as a white crystal. 1H-NMR (300 MHz, CDCL3, ) : 3.80 (3H, s), 5.44 (1H, s), 6.31 (1H, d, J=16 Hz), 6.85 (2xlH, d, J=8.5 Hz), 7.43 (2xlH, d, J=8.5 Hz), 7.64 (1H, d, J=16 Hz); MASS (ES-): m/e 177.
	Stage #1: methanol With thionyl chloride at 0℃; for 0.5h; Stage #2: p-Coumaric Acid In methanol for 1.5h; Heating / reflux;	106 Preparation 106 Thionyl chloride (1.75 mL) was dropwise added under stirring to methanol at 0° C. After 30 minutes 4-hydroxycinnamic acid (3.29 g) was added and the mixture was refluxed for 1.5 h. The solvent was evaporated in vacuo and the residue was crystalized from diisopropyl ether and hexane to give Compound (106) (2.41 g) as a white crystal. 1H-NMR (300 MHz, CDCl3, δ): 3.80 (3H, s), 5.44 (1H, s), 6.31 (1H, d, J=16 Hz), 6.85 (2×1H, d, J=8.5 Hz), 7.43 (2×1H, d, J=8.5 Hz), 7.64 (1H, d, J=16 Hz); MASS (ES-): m/e 177.
	With sulfuric acid for 2h; Reflux;	Synthesis of methyl p-coumarate (4), methyl caffeate (5), and methyl ferulate (6) The appropriate phenolic acid (100 mg) was dissolved in MeOH (50 ml) to which 3 drops of H2SO4 had been added. The solution was refluxed for 2 h, NaHCO3 (100 mg) was added, and the solvent was evaporated in vacuo at 40 °C. The residue was partitioned between Et2O (15 mL) and H2O (15 mL), the organic layer separated, dried (Na2SO4), and the solvent was evaporated in vacuo to afford the desired ester, as a white solid. The esters were used in the oxidation reaction without further purification.
	With sulfuric acid at 80℃; for 16h;	11.A [00324] Method A: A mixture of cinnamic acid (25 mmol) and concentrated H2S04 (0.1 ml_) in anhydrous MeOH (25 mL) was refluxed at 80¾ (bath temperature) for 16 h. After the excess MeOH was removed by a rotary evaporator, the residue was treated with H20 (50 mL), and the resulting mixture was extracted with EtOAc (3^50 mL). The combined extracts were washed with H20 (50 mL) and brine (50 mL), and dried (anhydrous Na2S04). The solvent was evaporated to dryness, and the crude products were purified by flash silica gel chromatography (eluting with 10-60% hexane in EtOAc) to afford methyl cinnamate. To an ice-cold solution of methyl cinnamate described above (8 mmol) dissolved in anhydrous MeOH (10 mL) and THF (10 mL) was added hydroxylamine hydrochloride (1.67g, 24 mmol, 3 equiv) followed by 25% sodium methoxide in methanol solution (8.4 mL, 36 mmol, 4.5 equiv). The reaction mixture was stirred under argon and at 0 for 2 h, then allowed to warm to ambient temperature with the stirring was continued overnight (16 h). The resulting yellow suspension was condensed to dryness with a rotary evaporator, and the residue was treated with 1 N HCI aqueous solution (30 mL). The mixture was extracted with EtOAc (3 <50 mL), and dried (anhydrous Na2S04). Evaporation of the solvent afforded the crude products (480 mg), which was purified by flash silica gel chromatography (eluting with 5-15% MeOH in DCM) to afford the hydroxamate.[00325] Using Method A, Compounds 103, 125, 129, 130, and 131 were synthesized. The carboxyl acid of PCA was converted to hydroxamite to synthesize compound 103 by reacting methyl ester 101 with hydroxylamine under basic conditions. Compound 103 was a light-brown solid, obtained at 25% yield (based on the methyl ester). The hydroxyl group of 103 was replaced by methoxy group, resulting in the hydroxamate 125. Compound 125 was light-brown solid, obtained at 67% yield. Compound 129 was light-brown solid, obtained at 21 % yield. Compound 130 was an off-white solid, obtained at 63% yield. Compound 131 was a grey solid, obtained at 25% yield. Identity of compounds was verified by H NMR (75 MHz, CD3OD).
	With acetyl chloride
280 g	With sulfuric acid for 5h; Reflux;	1 Example 1 First Step: (0174) trans-Coumaric acid (400 g) was added to methanol (1,200 ml) and concentrated sulfuric acid (10 g) was added dropwise, and the mixture was heated under reflux with stirring for 5 hours. After the reaction mixture had been cooled to room temperature, the methanol was distilled off under reduced pressure. The resulting residue was poured into ice-water (2,000 ml), and the mixture was extracted with ethyl acetate (2,000 ml). The combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate and water, and dried over anhydrous magnesium sulfate. The ethyl acetate was distilled off under reduced pressure, and the resulting residue was recrystallized from ethanol to give the compound (ex-1) (280 g).
15.6 g	With acetyl chloride at 0 - 75℃; for 5h;
	With sulfuric acid In methanol for 5h; Reflux;
	With sulfuric acid for 1h; Reflux;	Synthesis of cinnamic acid derivatives Zosteric acid was synthesized as already described in a previous work [16]. The cis isomer 38was obtained starting from cis 4-hydroxycinnamic acid 32 under microwave irradiation in thepresence of sulfur trioxide pyridine complex in acetonitrile (Fig 3). The final product was isolatedas sodium salt. Most of the substituted cinnamic acid derivatives were prepared in highyield (> 90%) by the Knoevenagel-Doebner procedure. In detail, compounds 2, 7, 8, 11 and 17were obtained through a one-pot reaction between the suitable substituted benzaldehyde andmalonic acid in refluxing pyridine to induce decarboxylation (Fig 4) [20]. The trans geometriesof the ethenyl π-bonds were confirmed by proton-proton coupling constants. Cis cinnamicacid 37 was synthesized from the commercially available ethyl phenylpropiolate. The subsequenthydrogenation of alkyne in the presence of the Lindlar catalyst and pyridine in methanolled to the corresponding cis-alkene 36. Then the ester group was hydrolyzed under alkaline conditions to provide the final compound 37 (Fig 5). Esters of cinnamic acid in cis (33) or intrans configuration (23, 24) were prepared by Fischer esterification of the carboxylic group[21]. The protection of the hydroxyl group as methyl ether in the presence of iodomethane indry N,N-dimethylformamide provided the compounds 35. The hydrolysis of the ester was performedin alkaline conditions to obtain compound 34 (Fig 3).
	With sulfuric acid for 12h; Reflux;	3.2. General Method for Synthesizing Compounds 5-12 General procedure: Ferulic acid (1) or trans-4-hydroxycinnamic acid (2) or isoferulic acid (3) or trans-3-hydroxycinnamic acid (4) and five drops of H2SO4 (95%) were refluxed in methanol or ethanol for 12 h. The reaction mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate. The organic layer was washed with a 5% aqueous NaHCO3 solution and water. After drying over anhydrous Na2SO4,the ethyl acetate was removed in vacuo. The residue was purified by column chromatography on silica gel using ethyl acetate/petroleum ether mixtures as eluents to afford compounds 5-12.
	With hydrogenchloride In water at 65℃;
280 g	With sulfuric acid for 5h; Reflux;	1.2 400 g of trans-p-coumaric acid was added to 1200 ml of methanol, 10 g of concentrated sulfuric acid was added dropwise, and the mixture was stirred under reflux for 5 hours. After cooling to room temperature, methanol was distilled off under reduced pressure. The obtained residue was poured into 2000 ml of ice water, 2000 ml of ethyl acetate And the organic layer was separated. The obtained organic layer was washed with saturated aqueous sodium bicarbonate and water, And dried over anhydrous magnesium sulfate. Ethyl acetate was distilled off under reduced pressure, The resulting residue was recrystallized from ethanol to obtain 280 g of Compound (ex-2).
	With sulfuric acid for 24h; Reflux;
	With thionyl chloride at 0 - 20℃; for 1h;	3.5.2. Preparation of M2 (methyl (E)-3-(4-((3,5,6-trimethylpyrazin-2-yl)methoxy)phenyl)acrylate)) To verify the accuracy of the proposed structure, we synthesized one of the metabolites, M2. Hydroxycinnamic acid (10.14 mmol) was added to anhydrous methanol (30 mL). After complete dissolution, thionyl chloride was slowly added dropwise under ice-cooling, while being stirred at 0 °C for 0.5 h, and then the temperature was slowly raised to room temperature. Then, the reaction solution was evaporated under reduced pressure. The reaction product was placed in a one-necked flask with potassium carbonate and N,N-dimethylformamide was added; the mixture was stirred at 65 °C for 3 h under nitrogen. Water was added to the reaction solution for dispersion before extraction with methylene chloride. After being evaporated, the residue was eluted with silica gel, and metabolite M2 was obtained. M2: m.p.: 124.0-124.4 °C. 1H-NMR (500 MHz, CDCl3) δ 7.64-7.61 (d, J = 7.6Hz, 1H, Ar-H), 7.46-7.44 (d, J = 7.4 Hz, 1H, Ar-H), 7.01-6.99 (d, J = 7.3 Hz, 1H, Ar-H), 6.31-6.28 (d, J = 6.3 Hz, 1H, Ar-H), 5.16 (s, 2H, -CH2), 3.78, 2.63 (s, 3H, -CH3), 2.57 (s, 3H, -CH3), 2.51 (s, 3H, -CH3) 13C-NMR (150 MHz, CDCl3) δ 167.92, 160.58, 151.73, 150.20, 148.92, 145.45, 144.61, 129.93, 127.80, 115.78, 115.64, 115.43, 70.22 (-CH2), 51.81 (-OCH3), 21.94 (-CH3), 21.65 (-CH3), 20.85 (-CH3), HR-MS (ESI) m/z: 313.16403 [M + H]+, calcd. for C18H20N2O3.
	With sulfuric acid for 24h; Reflux;
	With sulfuric acid for 48h; Reflux;	(E)-Methyl 3-(4-hydroxyphenyl)acrylate (13) Acid 12 (1.06 g 6.46 mmol) was dissolved in dry methanol. 2-3drops of conc. sulfuric acid were added and solution obtained was refluxedfor a two days until disappearing of starting material (controlledby TLC, CH2Cl2-acetic acid 100:1). After completion of the reactionmethanol was evaporated under vacuum. A residue was re-dissolved inethyl acetate (30 mL) and washed with water (10 mL), brine (10 mL)and dried over magnesium sulfate. Solvent was evaporated and theresidue was used in following step without further purification.White-off powder, 92% yield. 1H NMR (400 MHz, CDCl3) δ 3.81 (s,3H), 6.30 (d, J=16.0 Hz, 1H), 6.53 (br.s, 1H), 6.82-6.91 (m, 2H), 7.41(d, J = 8.6 Hz, 2H), 7.64 (d, J = 16.0 Hz, 1H).
	With acetyl chloride at 20℃; for 51h;

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2
[ 7400-08-0 ]
[ 6049-54-3 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1912,vol. 389,p. 36,111

3
[ 7400-08-0 ]
[ 501-98-4 ]

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4
[ 7400-08-0 ]
[ 3943-97-3 ]

Yield	Reaction Conditions	Operation in experiment
98%	With sulfuric acid In methanol Heating / reflux;	27.27a A mixture of 4-hydroxycinnamic acid (8.2 g, 50 mmol) and a drop OfH2SO4 in methanol (30 mL) was heated to reflux overnight. Then the solvent was evaporated, the residue was dissolved in ethyl acetate, washed with saturated NaHCO3 solution twice, brine, dried over MgSO4, concentrated to give the title compound 0501-66 as white solid (8.7 g, 98%): LCMS: 179 [M+l]+.
61%	With sulfuric acid In methanol; ethanol; water	1 4-Hydroxycinnamic Acid Methyl Ester (Compound 2a) Example 1 4-Hydroxycinnamic Acid Methyl Ester (Compound 2a) A solution of 4-hydroxycinnamic acid (compound 1a, 20.0 g, 0.12 mol) and 5 drops of concentrated sulfuric acid in 500 mL of reagent grade methanol was stirred for four days at 55° C., while monitored by TLC. The solvent was then removed from the reaction mixture on the rotovap and the solid residue was recrystallized from a mixture of 200 mL of ethanol and 200 mL of water to give 13.3 g of product in 61% yield: 13C NMR (75.4 MHz, CDCl3) δ 168.18, 157.88, 144.85, 129.95, 126.91, 115.86, 114.87, 51.81.
	With methanol; sulfuric acid

	Multi-step reaction with 4 steps 1: K₂CO₃ / dimethylformamide / Heating 2: aq. NaOH / methanol / 70 °C 3: K₂CO₃ / acetone / Heating 4: aq. HCl; AcOH / 70 °C
	With sulfuric acid In methanol; water	6.1 Synthesis of Compound (1c) 1) 25 g (0.152 mol) of p-hydroxycinnamic acid was dissolved in 100 ml of methanol, to which 1 g of concentrated sulfuric acid was added and refluxed for 8 hours. After allowing the system to cool down to room temperature, twice the amount of water was added thereto. The pellet was collected by filtration, washed with water, and dried. 25 g of a yellowish white solid was obtained. The solid was recrystallized from toluene. As a result, 21 g of methyl para-hydroxycinnamate was obtained as a yellowish white solid.
	Multi-step reaction with 2 steps 1: thionyl chloride / dichloromethane / 2 h / 20 °C / Reflux 2: dichloromethane / 3 h / Reflux
	Multi-step reaction with 2 steps 1: thionyl chloride / 2 h / 85 °C 2: triethylamine / 2 h / 20 °C

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5
[ 2538-87-6 ]
[ 7400-08-0 ]

Reference： [1],1938,vol. 11,p. 6
Chemisches Zentralblatt,1939,vol. 110,p. 1183

6
[ 80-69-3 ]
[ 7400-08-0 ]
(E)-p-coumaroyltartronic acid [ No CAS ]

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7
[ 57602-02-5 ]
[ 7400-08-0 ]
[ 130740-01-1 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1990,vol. 63,p. 1623 - 1628

8
[ 29588-94-1 ]
[ 136918-14-4 ]
[ 501-98-4 ]
[ 7400-08-0 ]
(S)-4-(4-Hydroxy-phenyl)-1,5-dioxo-2,3,4,5-tetrahydro-1H-benzo[c]azepine-3-carboxylic acid [ No CAS ]

Reference： [1]Tetrahedron,1994,vol. 50,p. 701 - 714

9
2-acetonyl-8-(6-O-coumaroyl-β-D-glucopyranosyl)-7-hydroxy-5-methylchromone [ No CAS ]
[ 40738-40-7 ]
[ 501-98-4 ]
[ 7400-08-0 ]
[ 104871-04-7 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1991,vol. 39,p. 704 - 708

10
chrysoeriol-7-O-β-D-(3''-E-p-coumaroyl)-glucopyranoside [ No CAS ]
[ 2280-44-6 ]
[ 7400-08-0 ]
[ 491-71-4 ]

Reference： [1]Phytochemistry,1986,vol. 25,p. 1253 - 1254

11
anisofolin-A [ No CAS ]
[ 7400-08-0 ]
[ 578-74-5 ]

Reference： [1]Heterocycles,1982,vol. 19,p. 1655 - 1662

12
[ 64-17-5 ]
[ 7400-08-0 ]
[ 2979-06-8 ]

Yield	Reaction Conditions	Operation in experiment
95%	With sulfuric acid; at 65℃; for 18h;	p-Cinnamic acid (2) (2.00 g, 12.2 mmol) was dissolved in 100 mL of ethanol containing 3.5 mL of concentrated H2SO4. The solution was refluxed at 65 C for 18h. After concentration under reduced pressure, the solution was diluted with ethyl acetate and washed with saturated aqueous NaHCO3 and brine. After drying over anhydrous Na2SO4, the volatiles were removed in vacuo. The raw products were purified by column chromatography on silica gel using EtOAc/petroleum ether (1/5) mixtures as eluents to afford (E)-ethyl 3-(4-hydroxyphenyl)acrylate (2.22 g, 95%) as white solid. 1HNMR(CDCl3, 400MHz) delta 1.34 (3H, t, J = 7.0Hz, -OCH2CH3), 4.27 (2H, q, J = 7.0Hz, -OCH2CH3), 6.29 (1H, d, J = 16.0Hz, -CH=CHCO-), 6.90 (2H, d, J = 8.0Hz, H-3, H-5 of Ph), 7.40 (2H, d, J = 8.4Hz, H-2, H-6 of Ph), 7.64 (1H, d, J = 16.0Hz, -CH=CHCO-), 7.70-7.56 (br, 1H, OH); MS (ESI) m/z: 193.1 (M + H)+. The spectroscopic data of (E)-ethyl 3-(4-hydroxyphenyl)acrylate were consistent with the reference.
75%	With sulfuric acid;Reflux;	In a 1 L three-necked flask,102.0 g of trans-p-coumaric acid,500 mL of ethanol,5.8 g of sulfuric acid,in addition,The mixture was stirred while heating under reflux.After completion of the reaction,Pour the reaction system into 3 L of water,After filtering the precipitate,The filtrate was dried,90.0 g of the desired product DA-4-1 (white solid) was obtained (yield: 75%).
68%	With thionyl chloride; at 0℃;Reflux; Inert atmosphere;	General procedure: Thionyl chloride (1.16 g, 1.5 equiv) was added drop-wise to a solution of acid (1.0 g, 1.0 equiv) in the corresponding alcohol (15 ml) at 0&d eg;C. The solution was refluxed under a nitrogen atmosphere until all starting material was consumed (TLC monitoring). Then the solvent was removed under vacuo and the residue was purified by silica gel column chromatography eluting with ethyl acetate/n-hexane to afford the corresponding carboxylic esters.

45%	With sulfuric acid; for 30h;Reflux;	General procedure: A series of 4- or 3-substituted ethyl-cinnamates was prepared by conventional method [38], using 2 mmol of para and meta substituted cinnamic acids refluxed in absolute ethanol (15 mL) and sulfuric acid (0.1 mL) for 30 h. The ester formation was monitored by GC and TLC (hexane:acetate 9:1 as eluent). The products were isolated after washing with aqueous sodium bicarbonate solution and solvent extraction with dichloromethane. After work up and solvent evaporation, most of the pure esters were obtained as an oil or a solid. All compounds were characterized by 1H and 13C-NMR spectroscopy, in agreement with the literature [39-41]. The spectroscopic and characterization information of all compounds is given as Electronic Supplementary Information.
	With sulfuric acid; for 5h;Heating / reflux;	(a) Trans-4-hydroxycinnamic acid (5.00g, 30.46mmol) was dissolved in ethanol (60ml), and sulfuric acid (1.6ml) was added thereto. The mixture was refluxed for 5 hours and then the solvent was evaporated out. The residue was diluted with water, neutralized with sodium hydrogencarbonate, and then extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over MgSO4, and then the solvent was evaporated out.
	With sulfuric acid; for 96h;Heating / reflux;	The ethyl (E)-4-hydroxycinnamate required as starting material was prepared as follows: [00109] A mixture of 10 g 4-hydroxycinnamic acid, 100 ml ethanol and 0.5 ml concentrated sulphuric acid was heated under gentle reflux for 96 hours. The reaction mixture was poured onto water, the resultant precipitate filtered off, washed with portions of water and then dried. The residue was purified by column chromatography on silica gel using ethyl acetate as eluent and recrystallisation from acetonitrile to yield 9.2 g of ethyl (E)-4-hydroxycinnamate.
	With thionyl chloride; for 24h;Reflux;	General procedure: To an icy solution of hydroxy cinnamic acid (10 mmol) in ethanol (30 mL) was added thionyl chloride (0.5 mL) dropwise. The reaction mixture was refluxed for 24 h to give the corresponding crude ethyl cinnamate.
	With sulfuric acid; for 12h;Reflux;	General procedure: Ferulic acid (1) or trans-4-hydroxycinnamic acid (2) or isoferulic acid (3) or trans-3-hydroxycinnamic acid (4) and five drops of H2SO4 (95%) were refluxed in methanol or ethanol for 12 h. The reaction mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate. The organic layer was washed with a 5% aqueous NaHCO3 solution and water. After drying over anhydrous Na2SO4,the ethyl acetate was removed in vacuo. The residue was purified by column chromatography on silica gel using ethyl acetate/petroleum ether mixtures as eluents to afford compounds 5-12.

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13
[ 7400-08-0 ]
[ 83392-10-3 ]
[ 177085-36-8 ]

Reference： [1]Helvetica Chimica Acta,1996,vol. 79,p. 548 - 559

14
[ 7400-08-0 ]
[ 85-61-0 ]
[ 30802-00-7 ]

Yield	Reaction Conditions	Operation in experiment
	With recombinant Selaginella moellendorffii 4-coumarate:coenzyme A ligase 1; ATP; magnesium chloride; In aq. buffer; at 30℃; for 0.5h;pH 7.5;Enzymatic reaction;Kinetics;	General procedure: We performed Sm4CLs enzyme assays to detect the formation of the <strong>[85-61-0]CoA</strong> esters of variouscinnamic acid derivatives. Each 200 muL assay contained 10 mug purified protein, 200 muMsubstrate, 5mMATP, 300 muM<strong>[85-61-0]CoA</strong>, and 5mMMgCl2, made up in 200mMTris-HCl buffer (pH 7.5). Enzymatic reactionswere incubated for 30 min at 30 C, and the reaction products were analyzed using a HPLC device(1260 Infinity Binary LC system, Agilent, Santa Clara, CA, USA), equipped with a multi wavelengthdetector. The samples were separated through a 5-mum reverse-phase XDB-C18 column with a flow rateof 1 mL/min. A linear gradient of solvent A (1% H3PO4 in H2O) and solvent B (CH3CN) were appliedas follows: 0-5 min, 5% B isocratic; 5-35 min, 5-25% B linear; 35-36 min, 25-100% B linear. Standardsolutions of reference compounds were used for calibration.The effects of pH and temperature on the enzyme activity were examined using p-coumaricacid as substrate. To determine optimal pH, enzymatic activity was assessed in 200 mM Tris-HClbuffer (pH 5.0, 6.0, 6.5, 7.0, 7.5, 8.0, 8.5, and 9.0), while the optimal temperature was determined bymeasuring enzymatic activity at 10, 20, 30, 40, 50, and 60 C. All experiments were performed intriplicate. Kinetic parameters were determined using different substrate concentrations. We performedthis experiment in triplicate, with 3 mug purified enzyme in a final volume of 200 muL of 200 mM Tris-HClbuffer at the optimal pH and temperature for 10 min. The level of UV absorption was recorded at1 min intervals. Relevant wavelengths were 311 nm (cinnamoyl <strong>[85-61-0]CoA</strong>), 333 nm (p-coumaroyl <strong>[85-61-0]CoA</strong>),346 nm (caffeoyl <strong>[85-61-0]CoA</strong>), 346 nm (feruloyl <strong>[85-61-0]CoA</strong>), and 352 nm (sinapoyl <strong>[85-61-0]CoA</strong>) [37,41,42]. For determiningkinetic properties with dihydro-p-coumaric acid, reactions were incubated at optimal temperature for10 min and analyzed using HPLC, and then the quantity of the reaction product present was estimatedfrom a standard calibration curve.

Reference： [1]Phytochemistry,1997,vol. 44,p. 605 - 608
[2]Journal of the American Chemical Society,2011,vol. 133,p. 20684 - 20687
[3]PLoS ONE,2016,vol. 11
[4]Molecules,2018,vol. 23
[5]Green Chemistry,2018,vol. 20,p. 3426 - 3431

15
(1R,3aS,5aS,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-Hydroxy-5a-[(E)-3-(4-hydroxy-phenyl)-acryloyloxymethyl]-1-isopropenyl-5b,8,8,11a-tetramethyl-icosahydro-cyclopenta[a]chrysene-3a-carboxylic acid [ No CAS ]
[ 501-98-4 ]
[ 7400-08-0 ]
(+)-cylicodiscic acid [ No CAS ]

Reference： [1]Phytochemistry,1998,vol. 47,p. 1367 - 1374

16
[ 7400-08-0 ]
[ 3417-91-2 ]
(E)-N-(4-hydroxycinnamoyl)tyrosine [ No CAS ]

Reference： [1]Phytochemistry,2000,vol. 54,p. 387 - 392

17
[ 7400-08-0 ]
(1R,2S,3R,4S)-3,4-Bis-(4-hydroxy-phenyl)-cyclobutane-1,2-dicarboxylic acid [ No CAS ]
[ 501-98-4 ]

Reference： [1]Organic Letters,2005,vol. 7,p. 529 - 532

18
[ 7400-08-0 ]
[ 74-88-4 ]
[ 3943-97-3 ]

Yield	Reaction Conditions	Operation in experiment
98%	With potassium hydrogencarbonate In N,N-dimethyl-formamide at 40℃;

Reference： [1]Guo, Wei; Li, Junfei; Fan, Ningjuan; Wu, Weiwei; Zhou, Peiwen; Xia, Chizhong [Synthetic Communications, 2005, vol. 35, # 1, p. 145 - 152]

19
[ 7400-08-0 ]
[ 149-73-5 ]
[ 3943-97-3 ]

Yield	Reaction Conditions	Operation in experiment
96%	With thionyl chloride In methanol at 20℃; for 48h;

Reference： [1]Pearson, Andrew G.; Kiefel, Milton J.; Ferro, Vito; Von Itzstein, Mark [Carbohydrate Research, 2005, vol. 340, # 13, p. 2077 - 2085]

20
[ 7400-08-0 ]
[ 85-61-0 ]
[ 30802-00-7 ]

Yield	Reaction Conditions	Operation in experiment
	With Piper nigrum 4-coumarate:CoA ligase isoform 1; ATP; magnesium chloride; In aq. buffer; at 25℃; for 0.75h;pH 7.5;Enzymatic reaction;Kinetics;	General procedure: The enzyme kinetic parameters were measured spectrophotometrically as described [22]. Each reaction contained 0.3 mM CoA, 2.5 mM MgCl2 and 2.5 mM ATP in 100 mM Tris-HCl (pH 7.5). For kinetic analyses, at least six concentrations of each substrate (coumaric, ferulic, 3,4-methylenedioxycinnamic, and piperic acids) ranging from 6.25 to 200 mM and 11 to 94 mg of each purified 4CL in a total volume of 1 ml reaction mixture were reacted in triplicate. For the assay of cinnamic acid, the acid concentration was between 15 mM and 600 mM and CoA was at 0.7 mM. The sample was set-up on ice and transferred to a water bath at 25C to equilibrate temperature for 1 min. The reaction was started by addition of CoA. The formation of the thioester products were followed at 311 nm for cinnamoyl-, 333 nm for 4-coumaroyl-, 346 nm for feruloyl-, 346 nm for 3,4-methylenedioxycinnamoyl-, and 368 nm for piperoyl-CoA, and the concentration of these products were calculated using the corresponding extinction coefficients of 22, 21, 19, 19, and 30.8 mM-1 cm-1, respectively [18,23,24]. To estimate the formation of 3,4-methylenedioxycinnamoyl-CoA, the same extinction coefficient, and lambdamax as feruloyl-CoA were extrapolated. The reaction was followed for 15 min until the linearity of the reaction was maintained. The reaction at 50 mM substrate concentration was allowed to proceed for another 30 min and then the mixture was stood in a boiling water bath for 3 min before scanning on spectrophotometer. Negative control was run with the combined, boiled enzymes, each at the same concentration as the individual reaction. Piperonylic acid was allowed to react for 45 min without kinetic measurement.

Reference： [1]Advanced Synthesis and Catalysis,2019,vol. 361,p. 5346 - 5350
[2]Phytochemistry,2005,vol. 66,p. 2072 - 2091
[3]Phytochemistry,2006,vol. 67,p. 2017 - 2029
[4]Phytochemistry,2008,vol. 69,p. 2449 - 2456
[5]Molecular BioSystems,2017,vol. 13,p. 598 - 606
[6]Biochemical Journal,2020,vol. 477,p. 61 - 74
[7]Biomolecules,2020,vol. 10

21
[ 7400-08-0 ]
[ 72784-43-1 ]
C₁₄H₁₅NO₄ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2785 - 2788

22
[ 7400-08-0 ]
[ 24807-40-7 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 3359 - 3368
[2]Bulletin of the Polish Academy of Sciences: Chemistry,1986,vol. 34,p. 115 - 122
[3]Patent: WO2008/147553,2008,A1

23
[ 7400-08-0 ]
[ 2538-87-6 ]

Reference： [1]Angewandte Chemie - International Edition,2006,vol. 45,p. 6317 - 6321
[2]Tetrahedron Letters,1984,vol. 25,p. 2755 - 2758

24
[ 7400-08-0 ]
[ 10210-17-0 ]

Yield	Reaction Conditions	Operation in experiment
82%	With whole cell cultures of dichomitus albidofuscus at 24℃; for 72h; Darkness; Microbiological reaction;	2.5. general procedure for preparative biotransformation General procedure: The substrate (1 mmol) was added to submerged cultures of DAL on the 3rd culture day. The reaction mixture was incubated on an incubation shaker at 150 rmin 1 (deflection 25 mm) under exclusion of light at 24 °C for 4 days. 10 g of NaCl was added to media, and the mixture was stirred for 10 min at 800 rpm (magnetic stirrer). For extraction, 50 mL of Et2O was added, and the resulting mixture was stirred for 20 min at 800 rpm (magnetic stirrer), and centrifuged for 5 min at 3000 × g to separatethe organic layer. The extraction was repeated three times. The combined organic layers were washed with brine (1 × 30 mL) and water (1× 30 mL), dried over Na2SO4 and evaporated to dryness. The resulting reaction mixtures were analysed by GC/MS and NMR spectroscopy.Products were purified by column chromatography on silica gel (eluent(pentane/ether) changed gradually: 10/1, 7/3, 1/1) to isolate the majorcomponents. The respective fractions were combined, concentrated in vacuum, and the 1H and 13C NMR spectra of the residuals were compared with those of reference compounds. Every biotransformation was repeated three times to verify the reproducibility of the experiments. The detailed information about experimental data and yields is provided in the Electronic Supplementary Information.
	Multi-step reaction with 3 steps 1: aq. HCl / 6 h / Heating 2: H₂ / 10percent Pd/C / methanol / 0.5 h / 760 Torr / Ambient temperature 3: LiBH₄ / diethyl ether; toluene / 0.25 h / Heating
	Multi-step reaction with 4 steps 1.1: pyridine / 1 h / 20 °C 2.1: chloroformic acid ethyl ester; triethylamine / 1,4-dioxane / 1 h / Inert atmosphere 2.2: 1 h / Inert atmosphere 3.1: potassium hydroxide / ethanol / 8 h / Inert atmosphere 4.1: 5%-palladium/activated carbon; hydrogen / ethyl acetate / 6 h / 20 °C / 2250.23 Torr

Reference： [1]Zhuk, Tatyana S.; Skorobohatko, Oleksandra S.; Albuquerque, Wendell; Zorn, Holger [Bioorganic Chemistry, 2021, vol. 108]
[2]Lam, Thi Bach Tuyet; Iiyama, Kenji; Stone, Bruce A. [Phytochemistry, 1992, vol. 31, # 4, p. 1179 - 1184]
[3]Current Patent Assignee: FUJIFILM HOLDINGS CORP.; DAINIPPON KASEI - JP2016/132639, 2016, A

25
[ 7400-08-0 ]
[ 144-55-8 ]
[ 2979-06-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; In ethanol;	Example 12 Synthesis of N-(1,2-diethyl-4-pyrazolidinyl)-4-geranyloxycinnamamide To a solution of 4- hydroxycinnamic acid (16.4 g) in ethanol (100 ml) was added sulfuric acid (10 ml). The mixture was refluxed with heating for 4 hours, Aqueous sodium bicarbonate solution was added to the reaction solution so as to make basic. Then, the reaction solution was extracted with chloroform. The extract was dried over sodium sulfate anhydride and then concentrated under a vacuum to yield a raw product of ethyl 4-hydroxycinnamate.

Reference： [1]Patent: US5849930,1998,A

26
[ 7400-08-0 ]
[ 95-12-5 ]
C₁₇H₁₈O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 0 - 20℃;	<EXAMPLE 3> Synthesis of the 2,3-epoxy-l-propoxy cinnamate norbornene (Formula 7) monomer 3-(l): 4-hydroxy cinnamate norbornene; The 4-hydroxy cinnamic acid (8.7 g, 53 mmol), norbornenemethanol (6.5 g, 52.4 mmol), EDC (Aldrich, Inc., 16 g, 84 mmol), and HOBT (Aldrich, Inc., 10.6 g, 78 mmol) were added to the 2-neck flask having the volume of 250 mi , and dissolved in 100 mi of DMF.After the temperature was reduced to 0C, triethylamine (Aldrich, Inc., 21 g, 0.21 mol) was slowly dropped thereon. After the reaction was performed overnight while the temperature was increasedto normal temperature, the reaction was finished and the extraction was performed by using a large amount of ethyl acetate. After thewashing was performed by using NaHCU3 and H2O and the drying was <n="38"/>performed by using anhydrous MgSO4, the filtration was performed toremove the solvent by using a rotary evaporator, thus creating theproduct. The purification was performed by using the column chromatography (Hexane : Ethyl acetate = 15 : 1) to obtain 9.9 g ofpure product (yield: 70%).

Reference： [1]Patent: WO2008/108592,2008,A1 .Location in patent: Page/Page column 36-37

27
[ 1135-24-6 ]
[ 140-10-3 ]
[ 331-39-5 ]
[ 7400-08-0 ]
[ 6099-04-3 ]
[ 537-73-5 ]
[ 20329-98-0 ]
[ 530-59-6 ]
[ 174472-00-5 ]
[ 640234-76-0 ]
[ 640234-75-9 ]
3-(4-hydroxy-3-(S)-methoxy-phenyl)-N-[2-(4-hydroxy-phenyl)-2-methoxy-ethyl]acrylamide [ No CAS ]
(E)-N-((S)-2-Methoxy-2-phenyl-ethyl)-3-phenyl-acrylamide [ No CAS ]
(E)-3-(3-Methoxy-phenyl)-N-((S)-2-methoxy-2-phenyl-ethyl)-acrylamide [ No CAS ]
(E)-3-(4-Hydroxy-phenyl)-N-((S)-2-methoxy-2-phenyl-ethyl)-acrylamide [ No CAS ]
(-)-aegeline O-methylether [ No CAS ]
(S)-N-(2-(4-hydroxyphenyl)-2-methoxyethyl)cinnamamide [ No CAS ]
(E)-3-(3-Hydroxy-4-methoxy-phenyl)-N-((S)-2-methoxy-2-phenyl-ethyl)-acrylamide [ No CAS ]
3-(4-hydroxyphenyl)-N-[2-(4-hydroxyphenyl)-2-methoxyethyl]acrylamide [ No CAS ]
(E)-N-[(S)-2-(4-Hydroxy-phenyl)-2-methoxy-ethyl]-3-(3-methoxy-phenyl)-acrylamide [ No CAS ]
(E)-3-(3,4-Dihydroxy-phenyl)-N-((S)-2-methoxy-2-phenyl-ethyl)-acrylamide [ No CAS ]
(E)-3-(4-Hydroxy-phenyl)-N-[(S)-2-methoxy-2-(4-methoxy-phenyl)-ethyl]-acrylamide [ No CAS ]
(E)-N-[(S)-2-Methoxy-2-(4-methoxy-phenyl)-ethyl]-3-(3-methoxy-phenyl)-acrylamide [ No CAS ]
(E)-3-(4-Hydroxy-3-methoxy-phenyl)-N-((S)-2-methoxy-2-phenyl-ethyl)-acrylamide [ No CAS ]
(S)-N-[2-(4-methoxyphenyl)-2-methoxyethyl]-3-(4-hydroxy-3-methoxyphenyl)acrylamide [ No CAS ]
(E)-3-(4-Hydroxy-3,5-dimethoxy-phenyl)-N-((S)-2-methoxy-2-phenyl-ethyl)-acrylamide [ No CAS ]
(E)-N-((S)-2-Methoxy-2-phenyl-ethyl)-3-(3,4,5-trimethoxy-phenyl)-acrylamide [ No CAS ]
(E)-3-(3-Hydroxy-4-methoxy-phenyl)-N-[(S)-2-methoxy-2-(4-methoxy-phenyl)-ethyl]-acrylamide [ No CAS ]
(E)-3-(3,4-Dihydroxy-phenyl)-N-[(S)-2-methoxy-2-(4-methoxy-phenyl)-ethyl]-acrylamide [ No CAS ]
(E)-3-(3-Hydroxy-4-methoxy-phenyl)-N-[(S)-2-(4-hydroxy-phenyl)-2-methoxy-ethyl]-acrylamide [ No CAS ]
(E)-3-(3,4-Dihydroxy-phenyl)-N-[(S)-2-(4-hydroxy-phenyl)-2-methoxy-ethyl]-acrylamide [ No CAS ]
(E)-N-[(S)-2-Methoxy-2-(4-methoxy-phenyl)-ethyl]-3-(3,4,5-trimethoxy-phenyl)-acrylamide [ No CAS ]
(E)-3-(4-Hydroxy-3,5-dimethoxy-phenyl)-N-[(S)-2-methoxy-2-(4-methoxy-phenyl)-ethyl]-acrylamide [ No CAS ]
(E)-N-[(S)-2-(4-Hydroxy-phenyl)-2-methoxy-ethyl]-3-(3,4,5-trimethoxy-phenyl)-acrylamide [ No CAS ]
(E)-3-(4-Hydroxy-3,5-dimethoxy-phenyl)-N-[(S)-2-(4-hydroxy-phenyl)-2-methoxy-ethyl]-acrylamide [ No CAS ]

Reference： [1]Patent: WO2005/44191,2005,A2 .Location in patent: Page/Page column 24; 25

28
[ 629-96-9 ]
[ 7400-08-0 ]
[ 112561-76-9 ]