40359-32-8|3-(Allyloxy)benzaldehyde| Ambeed

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Quality Control of [ 40359-32-8 ] Purity: 95% SDS Specification

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Product Details of [ 40359-32-8 ]

CAS No. :	40359-32-8
Formula :	C₁₀H₁₀O₂
M.W :	162.19
SMILES Code :	O=CC1=CC=CC(OCC=C)=C1
MDL No. :	MFCD04227161
InChI Key :	SEDRQGRABDFZKO-UHFFFAOYSA-N
Pubchem ID :	2716612

Safety of [ 40359-32-8 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 40359-32-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.1
Num. rotatable bonds	4
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	47.46
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	26.3 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.07
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.35
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.06
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	1.66
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.66
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.16

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.43
Solubility	0.6 mg/ml ; 0.0037 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.54
Solubility	0.465 mg/ml ; 0.00287 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-2.93
Solubility	0.192 mg/ml ; 0.00118 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.62 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	2.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.39

Application In Synthesis of [ 40359-32-8 ]

* 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.

Downstream synthetic route of [ 40359-32-8 ]

[ 40359-32-8 ] Synthesis Path-Downstream 1~35

1
[ 100-83-4 ]
[ 106-95-6 ]
[ 40359-32-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium carbonate; sodium iodide; In ethanol; for 3h;Reflux;	Example 1 . Preparation of 3-Allyloxybenzaldehyde; [0021] In a 1 L round bottomed flask equipped with mechanical stirrer, reflux condenser and thermometer were added 400 ml_ ethanol, 59.63 g of 3- hydroxybenzaldehyde (0.49 moles, 1 eq.), 7.3 g of sodium iodide (48 mmol, 0.1 eq.), 120.98 g of allyl bromide (0.59 moles, 1 .2eq.) and 101 .6 g of potassium carbonate (0.74 moles, 1 .25 eq.). The reaction mixture was heated to reflux and heating continued for three hours. Heating was then discontinued and the reaction was allowed to cool to room temperature. The mixture was then filtered through a Hyflosupercel pad and ethanol was removed by rotary evaporation. The residual oil was then taken up in 500 ml_ of MTBE and the organic phase washed sequentially with 10% aqueous sodium hydroxide, water and brine. After drying over sodium sulfate, filtration and rotary evaporation of solvent 79.7 g of a yellow oil of 3-allyloxybenzaldehyde (quantitative yield) was obtained.
100%	With potassium carbonate; In ethanol; for 3h;Reflux;	Example 1 . Preparation of 3-Allyloxybenzaldehyde 3; [0016] In a 1 L round bottomed flask equipped with mechanical stirrer, reflux condenser and thermometer was added in sequence 400 mL ethanol, 59.63 g of 3-hydroxybenzaldehyde (0.49 moles, 1 eq.), 7.3 g of sodium iodide (48 mmol, 0.1 eq.), 120.98 g of allyl bromide (0.59 moles, 1 .2eq.) and 101 .6 g of potassium carbonate (0.74 moles, 1 .25 eq.). The reaction mixture was heated to reflux and heating continued for three hours. Heating was then discontinued and the reaction was allowed to cool to room temperature. The mixture was then filtered through a Hyflosupercel pad and ethanol was removed by rotary evaporation. The residual oil was then taken up in 500 mL of MTBE and the organic phase washed sequentially with 10% aqueous sodium hydroxide, water and brine. After drying over sodium sulfate, filtration and rotary evaporation of solvent 79.7 g of a yellow oil of 3-allyloxybenzaldehyde (quantitative yield) was obtained.
100%	With potassium carbonate; sodium iodide; In ethanol; for 3h;Reflux;	In a 1 L round bottomed flask equipped with mechanical stirrer, reflux condenser and thermometer were added 400 mL ethanol, 59.63 g of 3-hydroxybenzaldehyde (0.49 moles,1 eq.), 7.3 g of sodium iodide (48 mmol, 0.1 eq.), 120.98 g of allyl bromide (0.59 moles,1.2 eq.) and 101.6 g of potassium carbonate (0.74 moles,1.25 eq.). The reaction mixture was heated to reflux and heating continued for three hours. Heating was then discontinued and the reaction was allowed to cool to room temperature. The mixture was then filtered through a Hyflosupercel pad and ethanol was removed by rotary evaporation. The residual oil was then taken up in 500 mL of MTBE and the organic phase washed sequentially with 10% aqueous sodium hydroxide, water and brine. After drying over sodium sulfate, filtration and rotary evaporation of solvent 79.7 g of a yellow oil of 3-allyloxybenzaldehyde (quantitative yield) was obtained.

98%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere;	General procedure: To a suspension ofphenol (16, 17, 22, and 23) (1 mmol, 1.0 equiv) and K2CO3(3 mmol, 3 equiv) in anhydrous DMF(5 mL) was added allylbromide (1.5 mmol, 1.5 equiv) dropwise under nitrogenatmosphere at room temperature. The mixture was stirred atroom temperature for 1 h. After completion of the reaction,water (10 mL) was added. The mixture was then extractedwith ether (2 × 30 mL), the combined organic layer waswashed with brine (2 × 30 mL), dried over anhydrousNa2SO4, filtered and the filtrate was concentrated in vacuo.The crude residue was purified by column chromatography (EtOAc/hexane = 1/8) to yield the allyl protected aldehyde(11, 18, 7, and 9).
98%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 1h;Inert atmosphere;	Phenol (16, 17, 22 and 23) (1 mmol, 1.0 eq.) And Allyl bromide (1.5 mmol, 1.5 eq.) Was added dropwise to a suspension of K2CO3 (3 mmol, 3 eq.) In anhydrous DMF (5 mL) under nitrogen atmosphere at room temperature. The mixture was stirred at room temperature for one hour. After completion of the reaction, water (10 ml) was added. The mixture was extracted with ether (2 x 30 mL) and the organic layer was washed with brine (2 x 30 mL), dried over anhydrous Na2SO4, filtered and the filtrate was concentrated in vacuo. The crude compound was purified by column chromatography (EtOAc / hexane = 1/8) to give aldehydes 11, 18, 7 and 9 protected with allyl groups.
98%	With 18-crown-6 ether; potassium carbonate; potassium iodide; In acetonitrile; at 75℃; for 18h;	To a stirred solution of 3-hydroxybenzaldehyde (8.0 g, 65.6 mmol) in acetonitrile (80 mL) was added allylbromide (11.0 mL, 131 mmol), KI (1.09 g, 6.56 mmol), 18-crown-6 (864 mg, 3.26 mmol) and K2CO3 (26.4 g, 191 mmol) at rt, after which the solution was refluxed at 75 C for 18 h. The K2CO3 was filtered off and the solvent was removed under reduced pressure·H2O (100 mL) was added and the aqueous layer extracted with EtOAc (2 * 100 mL). The organic layer was separated, washed with brine (50 mL), dried (Na2SO4) and the solvent removed under reduced pressure to yield the title compound as an orange oil, which was used without further purification (10.5 g, 64.4 mmol, 98%). Rf = 0.38 (5% EtOAc in hexane). IR: lambdamax = 2861 (w, C-H), 1681 (s, C=O), 1598 (s, C=C), 1483 (m, C=C), 1457 (m, C=C). 1H NMR (400 MHz, CDCl3): deltaH = 9.92 (1H, s, H10), 7.37-7.44 (2H, m, H6 & H7), 7.36 (1H, dd, J = 2.0, 1.0 Hz, H9), 7.15 (1H, dt, J = 7.2, 2.4 Hz, H5), 5.96-6.09 (1H, ddt, J = 17.2, 10.5, 5.2 Hz, H2), 5.40 (1H, dq, J = 17.3, 1.5 Hz, H1t), 5.28 (1H, dq, J = 10.6, 1.4 Hz, H1c), 4.55 (2H, dt, J = 5.3, 1.4 Hz, H3). 13C NMR (101 MHz, CDCl3): deltaC = 192.0 (C10), 159.1 (C4), 137.8 (C8), 132.7 (C2), 130.1 (C6), 123.5 (C7), 122.0 (C5), 118.0 (C1), 113.1 (C9), 68.9 (C3) . HRMS (ESI+): m/z found [M+H]+ 163.0751, C10H11O2 required 163.0754.
94.8%	With potassium carbonate; In N,N-dimethyl-formamide; at 25 - 45℃;	Meta hydroxy benzaldehyde (500 g) and potassium carbonate (679 g) were added to DMF (1000 ml). Allyl bromide (569.0 g) was gradually added to the reaction mixture, which was stirred at 25-45C. (0113) After completion of the reaction, water was added to the reaction mass followed by extraction with methyl tertiary butyl ether (MTBE). The organic layer was separated, washed with 1% sodium hydroxide solution (49 g NaOH in 490 ml water) to give compound (2). Yield: 630 g (94.8 %)
92%	With sodium perborate; In water; at 20℃; for 8.5h;Green chemistry;	General procedure: To the 25 mL round bottomed flask containing 5 mL of water, were added beta-Naphthol (1d, 0.50 g, 1 eq.), sodium perborate (3, 0.214 g, 0.4 eq.), and allyl bromide (2, 0.462 g, 1.1 eq.) and reaction mixture was stirred at room temperature as given time. Progress of the reaction was monitored by TLC. After completion of the reaction (6h), the product was extracted with ethyl acetate (3x15 mL) and combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude residue thus obtained was purified by silica gel column chromatography (100-200 mesh) to afford pure compound 4d. Similar procedure was adopted for the compounds 4a-c, and 4e-j.
89%	With caesium carbonate; In N,N-dimethyl acetamide; ethyl acetate;	EXAMPLE 58A 3-(allyloxy)benzaldehyde 3-Hydroxybenzaldehyde (1.00 g, 8.19 mmol) and allyl bromide (0.780 mL, 9.01 mmol) in N,N-dimethylacetamide (35 mL) was treated with Cs2CO3 (4.01 g, 12.3 mmol) and allowed to stir at room temperature for 12 hours. The reaction mixture was diluted with diethyl ether (150 mL), washed with 1N HCl, saturated NaHCO3, brine, dried (MgSO4), filtered and the filtrate concentrated. The residue was purified by flash chromatography (silica gel, using 7% ethyl acetate/hexanes as eluent) to provide the title compound as a clear oil (1.19 g, 89%). 1H NMR (CDCl3, 300 MHz) delta 4.82 (m, 2H), 5.25-5.5.50 (m, 2H), 6.03 (m, 1H), 7.18-7.52 (m, 4H), 9.95 (s, 1H); MS (DCI+) 163 (M+H)+.
83%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 3h;	General procedure: To a solution of 3-hydroxybenzaldehyde 1a (81.9 mmol, 10.0 g) and K2CO3 (1.5 g) in DMF (100.0 mL) was added allyl bromide (7.8 mL) and the mixture was stirred for 3 h at rt. The reaction mixture was quenched with water (50 mL) and the organic phase was extracted into Et2O (3×100 mL), dried over Na2SO4 and the solvent removed at reduced pressure to give a yellow liquid 2a (11.0 g, 83%): FTIR (KBr) 3071, 2818, 1697 cm-1; 1H NMR (200 MHz): delta 9.91 (s, 1H), 7.41 (m, 3H), 7.17 (m, 1H), 6.04 (m, 1H), 5.41 (dd, J 16.0, 6.0 Hz, 1H), 5.30 (dd, J 10.0, 6.0 Hz, 1H), 4.58 (d, J 5.6 Hz, 2H); 13C NMR (50 MHz, CDCl3): delta 191.7, 159.1, 137.7, 132.8, 130.1, 123.6, 122.1, 118.0, 113.1, 68.9; MS(EI) m/z: 162 (M+, 100), 147 (47), 121 (94), 65 (81).

References: [1]Organic and Biomolecular Chemistry,2004,vol. 2,p. 2461 - 2470.
[2]Patent: WO2012/9816,2012,A1 .Location in patent: Page/Page column 9-10.
[3]Patent: WO2012/9818,2012,A1 .Location in patent: Page/Page column 6.
[4]Patent: US2013/331593,2013,A1 .Location in patent: Paragraph 0032; 0033.
[5]Bulletin of the Korean Chemical Society,2015,vol. 36,p. 2907 - 2914.
[6]Patent: KR2016/115127,2016,A .Location in patent: Paragraph 0044; 0045.
[7]Bioorganic and Medicinal Chemistry,2017,vol. 25,p. 2825 - 2843.
[8]Organic Letters,2018,vol. 20,p. 7011 - 7014.
[9]Patent: WO2017/130109,2017,A1 .Location in patent: Page/Page column 25.
[10]European Journal of Organic Chemistry,2018,vol. 2018,p. 5605 - 5614.
[11]Organic and Biomolecular Chemistry,2019,vol. 17,p. 9489 - 9501.
[12]Journal of the American Chemical Society,1985,vol. 107,p. 1421 - 1423.
[13]Synthetic Communications,2015,vol. 45,p. 355 - 362.
[14]Patent: US2002/173665,2002,A1 .
[15]Chemical Communications,2012,vol. 48,p. 3303 - 3305.
[16]Journal of Chemical Research, Miniprint,1981,p. 2564 - 2572.
[17]Arkivoc,2017,vol. 2017,p. 194 - 209.
[18]Tetrahedron,2000,vol. 56,p. 1873 - 1882.
[19]Patent: US2667509,1951, .
[20]Il Farmaco,2003,vol. 57,p. 909 - 916.
[21]Journal of Organic Chemistry,2003,vol. 68,p. 1146 - 1149.
[22]Synlett,2012,vol. 23,p. 867 - 872.

2
[ 637-81-0 ]
[ 40359-32-8 ]
ethyl 2-azido-3-(3-allyloxyphenyl)propeonate [ No CAS ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1984,p. 1333 - 1337.

3
[ 40359-32-8 ]
[ 93799-49-6 ]
2,2,5,5-Tetramethyl-2,5-dihydro-1H-pyrrole-3-carboxylic acid (3-[1-(3-allyloxy-phenyl)-meth-(E)-ylidene]-amino}-propyl)-amide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 1138 - 1152.

4
[ 40359-32-8 ]
[ 79950-42-8 ]

Yield	Reaction Conditions	Operation in experiment
33.3%	In decalin; at 180 - 190℃;	Compound (2) (600 g) was added to decahydronaphthalene (1800 ml) and the stirred reaction mixture was heated to 180 to 190 0C. Stirring was continued till completion of the reaction as monitored by HPLC. After completion, the reaction mixture was cooled and acetonitrile (4200 ml) was added to it. The acetonitrile layer was separated, concentrated. Toluene was added to the residue. The resulting mass was cooled, filtered. Optional treatment of the solid thus obtained using mixture of ethyl acetate and cyclohexane gave compound (3). Yield: 200 g (33.3%)
	In decalin; at 217℃; for 7h;Inert atmosphere;	Example 2. Preparation of 2-allyl-3-hvdroxy-benzaldehyde; [0022] In a 500 ml three-necked Morton flask equipped with mechanical stirrer, thermometer and reflux condenser was added 100 g of <strong>[40359-32-8]3-allyloxybenzaldehyde</strong> (0.62 moles, 1 eq.) and 150 g of cis/trans decalin (1 .5 vol). The mixture was purged with nitrogen and then heated to a reflux temperature of 217C. The reaction was maintained at this reflux temperature for seven hours then cooled and added of 231 mL of toluene. The reaction mixture was then allowed to cool to room temperature. After stirring for 18 hours and further cooling to 0-5 C for 1 -2 hours, reaction mixture was filtered and the cake washed with 200 mL of heptane. The wet cake was stirred in 200 mL of heptane for 1 -2 hours at room temperature. After filtration and drying of the cake at 40 C, 54.27 g of crude 2-allyl-3-hydroxy-benzaldehyde were obtained. This represents a recovery of 82% of the available 2-allyl product produced by the Claisen rearrangement.
	In decalin; at 217℃; for 7h;Inert atmosphere;	Example 2. Preparation of 2-allyl-3-hvdroxy-benzaldehyde 4; - 6 - 75907-27 (KB) [0017] In a 500 ml three-necked Morton flask equipped with mechanical stirrer, thermometer and reflux condenser was added 100 g of <strong>[40359-32-8]3-allyloxybenzaldehyde</strong> (0.62 moles, 1 eq.) and 150 g of cis/trans decalin (1 .5 vol). The mixture was purged with nitrogen and then heated to a reflux temperature of 217C. The reaction was maintained at this reflux temperature for seven hours then cooled and 231 mL of toluene was added.. The reaction mixture was then allowed to cool to room temperature. After stirring for 18 hours and further cooling to 0-5 C, reaction mixture was filtered and the cake washed with 200 mL of heptane. The wet cake was stirred in 200 mL of heptane for 1 -2 hours at room temperature. After filtration and drying of the cake at 40 C, 54.27 g of crude 2-allyl-3-hydroxy- benzaldehyde were obtained. This represents a recovery of 82% of the available 2-allyl product produced by the Claisen rearrangement.

In decalin; at 217℃; for 7h;Inert atmosphere;

In a 500 ml three-necked Morton flask equipped with mechanical stirrer, thermometer and reflux condenser was added 100 g of <strong>[40359-32-8]3-allyloxybenzaldehyde</strong> (0.62 moles,1 eq.) and 150 g of cis/trans decalin (1.5 vol). The mixture was purged with nitrogen and then heated to a reflux temperature of 217 C. The reaction was maintained at this reflux temperature for seven hours then cooled and added of 231 mL of toluene. The reaction mixture was then allowed to cool to room temperature. After stirring for 18 hours and further cooling to 0-5 C. for 1-2 hours, reaction mixture was filtered and the cake washed with 200 mL of heptane. The wet cake was stirred in 200 mL of heptane for 1-2 hours at room temperature. After filtration and drying of the cake at 40 C., 54.27 g of crude 2-allyl-3-hydroxy-benzaldehyde were obtained. This represents a recovery of 82% of the available 2-allyl product produced by the Claisen rearrangement.

References: [1]Organic Letters,2018,vol. 20,p. 7011 - 7014.
[2]Patent: WO2017/130109,2017,A1 .Location in patent: Page/Page column 25; 26.
[3]Journal of the American Chemical Society,1985,vol. 107,p. 1421 - 1423.
[4]Patent: WO2012/9816,2012,A1 .Location in patent: Page/Page column 10.
[5]Patent: WO2012/9818,2012,A1 .Location in patent: Page/Page column 6-7.
[6]Patent: US2013/331593,2013,A1 .Location in patent: Paragraph 0034; 0035.

5
[ 40359-32-8 ]
[ 79950-42-8 ]
[ 79950-43-9 ]

Yield	Reaction Conditions	Operation in experiment
47%	In tetralin; at 180 - 182℃;Microwave irradiation;	To a 3000 ml one neck, round bottom flask equipped with a condenser and thermometer was added allylether (7) (308 g) and tetrahydronaphthalene (300 mL). This reaction mixture was heated slowly up to 180-182° C. (ramped the temp. in 5-10 minutes, internal temperature) in a microwave (power: 1500 Watts) and was kept at this temperature while stirring for 7-8 h. At this stage the reaction mixture turned brown and the reaction mixture was cooled to room temperature followed by cooling at 0 to 5° C. for 30 minutes. The solid was filtered and dried to obtain off-white solid (3-hydroxy-2-allylbenzaldehyde, 8) 145.5 g (47percent).

References: [1]Patent: US2016/107973,2016,A1 .Location in patent: Paragraph 0034; 0035; 0036.
[2]Journal of the Chemical Society. Perkin transactions I,1981,p. 2677 - 2679.
[3]Organic and Biomolecular Chemistry,2004,vol. 2,p. 2461 - 2470.
[4]Synlett,2012,vol. 23,p. 867 - 872.
[5]Tetrahedron Letters,2012,vol. 53,p. 2125 - 2128.
[6]European Journal of Organic Chemistry,2018,vol. 2018,p. 5605 - 5614.

6
[ 917-64-6 ]
[ 40359-32-8 ]
[ 79250-49-0 ]

References: [1]Journal of Chemical Research, Miniprint,1981,p. 2564 - 2572.

7
[ 40359-32-8 ]
[ 100-83-4 ]

References: [1]Journal of Chemical Research, Miniprint,1981,p. 2564 - 2572.
[2]Journal of Organic Chemistry,2003,vol. 68,p. 1146 - 1149.

8
[ 38697-17-5 ]
[ 106-95-6 ]
[ 40359-32-8 ]

References: [1]Bulletin des Societes Chimiques Belges,1994,vol. 103,p. 691 - 694.

9
[ 40359-32-8 ]
[ 14205-39-1 ]
[ 166392-23-0 ]

References: [1]ACH - Models in Chemistry,1994,vol. 131,p. 363 - 376.

10
[ 40359-32-8 ]
3-Allyloxy-4-[(3-allyloxy-phenyl)-hydroxy-methyl]-benzaldehyde [ No CAS ]

References: [1]Journal of Organic Chemistry,1997,vol. 62,p. 4643 - 4649.

11
[ 40359-32-8 ]
[ 34905-07-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium borohydrid; In methanol; acetic acid;	(B) To a solution of <strong>[40359-32-8]3-allyloxybenzaldehyde</strong> (7.2 g) in methanol (50 ml) at 0 C. was added sodium borohydride (1 g) in portions. The mixture was stirred for 30 minutes, evaporated dissolved in 5% acetic acid and extracted with diethyl ether (3100 ml), washed with water (2100 ml), and sodium bicarbonate (2*100 ml), dried (magnesium sulphate), filtered and evaporated to give 3-allyloxybenzyl alcohol (7.26 g).

References: [1]Tetrahedron,2000,vol. 56,p. 1873 - 1882.
[2]Patent: US5811459,1998,A .

Yield	Reaction Conditions	Operation in experiment
78%	With potassium carbonate; In acetone; at 20℃; for 24h;	General procedure: A solution of 35a (260.5 mg, 1.308 mmol) in acetone (20 mL) was subsequently treated with potassium carbonate (903.8 mg, 6.539 mmol) and allylbromide (340 mu, 3.924 mmol). After stirring at RT for 24 h, the reaction was quenched with water (20 mL). The aqueous layer was extracted with dichloromethane (2 x 30 mL). The organics were combined, filtered through a phase separator and the volatiles were removed in vacuo. The residue was purified by silica gel chromatography using a 25 g Isolute cartridge eluted with a continuous gradient of iso- hexanes/ethyl acetate 1 :0 to 3:2 to afford the title compound (289.7 mg, 92%) as a colorless oil
	With potassium carbonate; In acetonitrile; for 2h;Reflux;	General procedure: To a solution of2-hydroxybenzaldehyde (15 g, 123 mmol, 1 equiv) and allylbromide (11.7 mL, 135 mmol, 1.1 equiv) in MeCN (250 mL) was added K2C03 (23.8 g, 172 mmol, 1.4 equiv). The yellow slurry was then heated to reflux. After 2 h, TLC indicated complete conversion. The now pale cream colored mixture was removed from heat and filtered. The filtrate was concentrated invacuo to provide 2-(allyloxy)benzaldehyde (19.15 g, 96%) as a yellow oil. 1H NMR (400 MHz, CDCl3) 8 10.64- 10.49 (m, 1H), 7.86 (dd, J = 7.7, 1.9 Hz, 1H), 7.61 -7.49(m, 1H), 7.11-6.90(m,2H),6.10(ddt,J= 17.3, 10.5,5.2Hz, 1H),5.47(dq,J=17.3, 1.5 Hz, 1H), 5.36 (dq, J = 10.5, 1.4 Hz, 1H), 4.68 (dt, J = 5.1, 1.6 Hz, 2H).

13
[ 5651-87-6 ]
[ 40359-32-8 ]

References: [1]Journal of Organic Chemistry,2001,vol. 66,p. 5624 - 5626.

14
[ 40359-32-8 ]
[ 104-94-9 ]
[ 861227-10-3 ]

References: [1]Organic Letters,2001,vol. 3,p. 2461 - 2464.
[2]Patent: WO2005/70414,2005,A1 .Location in patent: Page/Page column Fig. 3; 5.

15
[ 100-83-4 ]
[ 107-18-6 ]
[ 40359-32-8 ]

References: [1]Chemistry - A European Journal,2001,vol. 7,p. 3798 - 3823.

16
[ 40359-32-8 ]
[ 507-09-5 ]
[ 383424-00-8 ]

References: [1]Chemistry - A European Journal,2001,vol. 7,p. 3798 - 3823.

17
[ 40359-32-8 ]
[ 151-50-8 ]
[ 108-24-7 ]
acetic acid (3-allyloxy-phenyl)-cyano-methyl ester [ No CAS ]

References: [1]Chemistry Letters,2003,vol. 32,p. 366 - 367.

18
[ 40359-32-8 ]
[ 108-24-7 ]
acetic acid acetoxy-(3-allyloxy-phenyl)-methyl ester [ No CAS ]

References: [1]Synlett,2006,p. 2719 - 2722.
[2]Tetrahedron Letters,2006,vol. 47,p. 5573 - 5576.
[3]Australian Journal of Chemistry,2007,vol. 60,p. 590 - 594.
[4]Chemistry Letters,2003,vol. 32,p. 366 - 367.
[5]Journal of the Chinese Chemical Society,2007,vol. 54,p. 489 - 492.

19
[ 503-87-7 ]
[ 40359-32-8 ]
(Z)-5-[(3-allyloxy)benzylidene]-2-thiohydantoin [ No CAS ]

References: [1]Il Farmaco,2003,vol. 57,p. 909 - 916.

20
[ 100-83-4 ]
[ 107-05-1 ]
[ 40359-32-8 ]

References: [1]Il Farmaco,2003,vol. 57,p. 909 - 916.

21
[ 40359-32-8 ]
[ 107-21-1 ]
1,1-ethylenedioxy-1-(3-allyloxy)methane [ No CAS ]

References: [1]Advanced Synthesis and Catalysis,2004,vol. 346,p. 446 - 450.

22
1,1-ethylenedioxy-1-(3-allyloxy)methane [ No CAS ]
[ 40359-32-8 ]

References: [1]Advanced Synthesis and Catalysis,2004,vol. 346,p. 446 - 450.

23
2-(3-(allyloxy)phenyl)-1,3-dithiane [ No CAS ]
[ 40359-32-8 ]

Yield	Reaction Conditions	Operation in experiment
	With eosin y; In water; acetonitrile; at 20℃; for 4h;Irradiation;	General procedure: To a clean screw-top vial (25 mL) equipped with a stir bar was added Eosin Y (1 mol%), thioacetal 1 (1 equiv., 0.2 mmol), H2O(0.3 mL), and acetonitrile (1.7 mL). The reaction mixture was stirred vigorously for 2-8 h under the irradiation with 45W CFL bulbin open air. The crude reaction mixture was quenched by the addition of water (15 mL) and further extracted with ethyl acetate (3 15 mL). The combined organic layers was dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum.The residue was further purified by column chromatography over silica gel using ethyl acetate and pet. ether as eluent to afford the desired product 2.

References: [1]Journal of Chemical Research,2005,p. 218 - 221.
[2]Synlett,2004,p. 659 - 662.
[3]Tetrahedron Letters,2020,vol. 61.

24
[ 40359-32-8 ]
[ 106-95-6 ]
4-allyl-3-allyloxybenzaldehyde [ No CAS ]
2-allyl-3-allyloxybenzaldehyde [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2004,vol. 2,p. 2461 - 2470.
[2]Synlett,2012,vol. 23,p. 867 - 872.

25
[ 40359-32-8 ]
[ 106-95-6 ]
[ 777079-77-3 ]

References: [1]Organic and Biomolecular Chemistry,2004,vol. 2,p. 2461 - 2470.

26
[ 40359-32-8 ]
[ 3300-51-4 ]
[ 864148-10-7 ]

References: [1]Journal of Organic Chemistry,2005,vol. 70,p. 6775 - 6781.

27
[ 40359-32-8 ]
[ 2393-23-9 ]
[ 864148-09-4 ]

References: [1]Journal of Organic Chemistry,2005,vol. 70,p. 6775 - 6781.

28
[ 40359-32-8 ]
[ 100-46-9 ]
[ 371754-67-5 ]

References: [1]Journal of the American Chemical Society,2001,vol. 123,p. 9692 - 9693.

29
[ 40359-32-8 ]
[ 104-94-9 ]
(3-allyloxy-benzylidene)-(4-methoxy-phenyl)-amine [ No CAS ]