Methyl(p-formylphenyl)acetate Chemical Properties

Boiling point:

285℃

Density 

1.157

Flash point:

124℃

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

Appearance

Off-white to yellow Solid

InChI

InChI=1S/C10H10O3/c1-13-10(12)6-8-2-4-9(7-11)5-3-8/h2-5,7H,6H2,1H3

InChIKey

YPJYQGMVBYQTTA-UHFFFAOYSA-N

SMILES

C1(CC(OC)=O)=CC=C(C=O)C=C1

Safety Information

HS Code 

2918290090

Methyl(p-formylphenyl)acetate Usage And Synthesis

Synthesis

General procedure for the synthesis of methyl 4-formylphenylacetate from methyl 2-(4-(hydroxymethyl)phenyl)acetate: a solution was formed by dissolving Dess-Martin Periodinane (1.5 eq.) in dichloromethane (0.3 M) at room temperature and protected by nitrogen with stirring. Subsequently, a dichloromethane (0.2 M) solution of methyl 2-(4-(hydroxymethyl)phenyl)acetate was added to this solution. After the reaction was carried out for 4 hours, the reaction mixture was diluted with ether (0.1 M). Next, the reaction mixture was poured into a saturated sodium bicarbonate (0.5 M) solution containing sodium thiosulfate (10.5 equivalents) and stirred for 30 minutes. The organic and aqueous phases were separated and the organic phase was washed sequentially with saturated sodium bicarbonate solution (1 liter), water (1 liter) and brine (1 liter). The washed organic phase was dried with sodium sulfate, filtered and concentrated in vacuum to afford the target product methyl 4-formylphenylacetate in 94% yield. The product was characterized by 1H NMR (400 MHz, CDCl3): δ 10.00 (s, 1H), 7.86 (d, 2H), 7.46 (d, 2H), 3.72 (m, 5H).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 10, p. 2647 - 2652
[2] Patent: US2004/254156, 2004, A1. Location in patent: Page 22
[3] Patent: WO2013/149997, 2013, A1. Location in patent: Page/Page column 47
[4] Patent: WO2014/86924, 2014, A1. Location in patent: Page/Page column 74; 75
[5] Patent: WO2007/106016, 2007, A1. Location in patent: Page/Page column 68

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