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CAS No. : | 17253-11-1 | MDL No. : | MFCD00066923 |
Formula : | C10H10O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BVRNERFWPQRVJB-UHFFFAOYSA-N |
M.W : | 194.18 | Pubchem ID : | 87020 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H319 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | 2-(2,3-dihydrobenzo[b] [l,4]dioxin-6-yl)acetic acid (S10-2).; A mixture of 1 ,4- benzodioxan-6-yl methyl ketone (SI 0-1; 5.5 g, 30.9 mmol), sulfur (1.98 g, 61.8 mmol) and morpholine (6.73 g, 6.76 mL, 77.3 mmol) was refluxed at 140C for 14 h. After cooling to rt, the reaction mixture was diluted with 150 mL of CH2C12, transferred to a seperatory funnel and washed with 25 mL of ice-cold brine. The aqueous layer was further extracted with CH2C12 (2 x 75 mL). The organic layers were combined, dried with Na2S04, and filtered. Activated charcoal was added to the filtrate and after several minutes was filtered and concentrated to give 12.7 g of a brown oil. A mixture of this in 75 mL of 10% KOH (ag.) was refluxed for 12h. After cooling the reaction mixture was transferred to a seperatory funnel and washed with ether (30 mL), The aqueous layer was acidified with 6N HC1 (~25 mL) to pH 2 and extracted with CH2C12 (4 x 100 mL). The organic layers were combined, washed with distilled water (100 ml), dried with Na2S04 and filtered. This was treated with charcoal, filtered, and solvent removed under reduced pressure and the resulting residue was purified by chromatography (hexane:EtOAc, 90:10 to 70:30) to give 3.90 g (65%) of S10-2. 1H NMR (500 MHz, CDC13) delta 6.80-6.82 (m, 2H), 6.74 (dd, J= 2.0, 8.2 Hz, 1H), 4.24 (s, 4H), 3.53 (s, 2H); MS (ESI) m/z 195.1 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | Step-c product (50 g, 0.24 mol) was added portion wise to hydrazine hydrate (69.7 g (67.6 ml), 5 eq) at 00C. Contents were heated to 8O0C and potassium hydroxide (30 g, 2.3 eq) was added portion wise. Overall reaction mixture was heated to 1100C and maintained for overnight at the same temperature. Progress of the reaction was monitored by TLC (50% ethyl acetate/hexane, Rf-0.7). On completion of the reaction, reaction contents were diluted with water (100 ml). Then the contents were acidified to a pH~3-4 with diluted HCI at 0C, solid thrown out was filtered and dried to yield the required product as a white solid (40 g, 85% yield, mp 79 - 82C). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 18h; | General procedure: A mixture 2-amino-4,5-dimethylthiophene-3-carboxamide (340 mg, 2 mmol), 2-(1-naphthalen-1-yl)acetic acid (372 mg, 2 mol), EDC (458 mg, 2.4 mmol), HOBt (324 mg, 2.4 mmol), DIEA ( 1.1 mL, 6 mmol) in DMF (10 mL) was stirred at room temperature for 18 h. The reaction mixture was poured into 100 mL of water then extracted with ethyl acetate (150 mL). The organic layer was washed with saturated NaHCO3 solution (3 x 50 mL), brine (3 x 50 mL), water (3 x 50 mL) respectively. The ethyl acetate layer was dried over MgSO4 and concentrated. The residue was chromatographed over silica gel (30 to 40% ethyl acetate in haxane) to afford compound 1 (277 mg, 41%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With potassium carbonate In ethylene glycol at 120℃; for 4.5h; Inert atmosphere; | 120.1 Step 1. 2-(2,3-dihydrobenzo[b][1,4]dioxacyclohexene-6-yl)acetic acid (GEN1-159-1) 1,2-dibromoethane (1.13 g, 6.0 mmol) was added to a solution of 2-(3,4-dihydroxyphenyl)acetic acid (500 mg, 3.0 mmol) and K2CO3 (1.24 g, 9.0 mmol) in ethylene glycol (5.0 mL). The resulting mixture was stirred at 120°C for 4.5 hours under a N2 atmosphere. The reaction mixture was cooled to room temperature and diluted with water (40 mL). EtOAc (40 mL) was added and the mixture was stirred for 5 minutes. The organic layer was discarded, and the aqueous layer was acidified with 2M HCl to pH <1. The aqueous layer was extracted with EA (60 mL*3). The combined organic layer was washed with water (150 mL), brine (150 mL), dried over Na2SO4 and it was concentrated to obtain a black oil. The crude product was purified by silica gel column chromatography and eluted with (EA/(PE + EA)=60%) to obtain the desired compound (495 mg, yield 85%) as a black oil. MS (ESI): Rt = 1.01 min, m/z 217 [M+Na]+, Purity: 100% 254 nm, 100% 214 nm. |
52% | With potassium carbonate In ethylene glycol at 120℃; for 4.5h; | 7 3,4-Ethylenedioxyphenylacetic acid (11) and 3,4-propylenedioxyphenylacetic acid (12) To a solution of 3,4-dihydroxyphenylacetic acid (500mg, 3.0mmol) and either 1,2-dibromoethane (1.13g, 6.0mmol) or 1,3-dibromopropane (1210mg, 6.0mmol) in ethylene glycol (5mL) was added anhydrous K2CO3 (1240mg, 9.0mmol). After heating at 120°C for 4.5h, the mixtures were cooled, diluted with H2O (50mL), acidified to pH N HCl), and extracted with EtOAc (3×20mL). The organic layers were concentrated under reduced pressure, and residues were purified by column chromatography (EtOAc/ Hexane=50:50 for 11; 40:60 for 12) to give 1144 (301mg, 52%) or 1245 (260mg, 42%). 11 1H NMR: (300MHz, CDCl3, δ) 3.56 (s, 2H, CH2), 4.23 (s, 4H, CH2), 6.75-6.87 (m, 3H, CH), 11.64 (br s, 1H, -COOH). 12 1H NMR: (250MHz, CDCl3, δ) 2.19 (app p, 2H, J=7.5Hz, CH2), 3.55 (s, 2H, CH2), 4.21 (m, 4H, CH2), 6.81-6.95 (m, 3H, CH), 10.50 (br s, 1H, -COOH). |
With potassium carbonate | 120.1 Step 1. Step 1. 2-(2,3-dihydrobenzo[b][1,4]dioxacyclohexene-6-yl)acetic acid (GEN1-159-1) 1,2-dibromoethane (1.13 g, 6.0 mmol) was added to a solution of 2-(3,4-dihydroxyphenyl)acetic acid (500 mg, 3.0 mmol) and K2CO3 (1.24 g, 9.0 mmol) in ethylene glycol (5.0 mL). The resulting mixture was stirred at 120°C for 4.5 hours under a N2 atmosphere. The reaction mixture was cooled to room temperature and diluted with water (40 mL). EtOAc (40 mL) was added and the mixture was stirred for 5 minutes. The organic layer was discarded, and the aqueous layer was acidified with 2M HCl to pH <1. The aqueous layer was extracted with EA (60 mL*3). The combined organic layer was washed with water (150 mL), brine (150 mL), dried over Na2SO4 and it was concentrated to obtain a black oil. The crude product was purified by silica gel column chromatography and eluted with (EA/(PE + EA)=60%) to obtain the desired compound (495 mg, yield 85%) as a black oil. MS (ESI): Rt = 1.01 min, m/z 217 [M+Na]+, Purity: 100% 254 nm, 100% 214 nm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With borane-THF In tetrahydrofuran at 0 - 20℃; for 2h; | 2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)ethanol 2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)ethanol BH3.THF (44 mL, 44 mmol, 1 M/THF) was added to a 0° C. solution of 2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)acetic acid (3.419 g, 17.6 mmol) in THF (8.8 mL). The reaction was allowed to warm to room temperature and after 2 h, 20 mL H2O was added slowly by syringe. The resulting mixture was extracted with ethyl acetate, the organic portion was washed with brine, and then was dried (Na2SO4), filtered and evaporated. Purification by flash chromatography (ethyl acetate/hexanes) gave the title compound (3.059 g, 99%). |
94% | With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 5h; Inert atmosphere; | |
88% | With borane-THF In tetrahydrofuran at 20℃; for 3h; Inert atmosphere; | 4.1.41. 2-(2-Chloro-4-methoxyphenyl)ethanol (13a) General procedure: To a solution of (2-chloro-4-methoxyphenyl)acetic acid (1.50 g,7.48 mmol) in THF (20 mL) was added 0.9 M BH3-THF complex inTHF solution (10.8 mL, 9.72 mmol). After stirring at room temperaturefor 3 h, MeOH (10 mL) was added, and the reaction mixturewas stirred at room temperature for 30 min and concentrated invacuo. The residue was purified by silica gel chromatography using26 47% EtOAc/hexane as eluent to give 1.44 g (quant.) of the titlecompound as a colorless oil. |