methyl (4-formylphenoxy)acetate Chemical Properties

Melting point:

40-42 °C

Boiling point:

315.2±17.0 °C(Predicted)

Density 

1.201±0.06 g/cm3(Predicted)

storage temp. 

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

Safety Information

HazardClass 

IRRITANT

HS Code 

2918999090

methyl (4-formylphenoxy)acetate Usage And Synthesis

Synthesis

General procedure for the synthesis of methyl (4-formylphenoxy)acetate from p-hydroxybenzaldehyde and methyl bromoacetate: K2CO3 (5.43 g, 39.3 mmol) was added to a solution of 4-hydroxybenzaldehyde (3.0 g, 25 mmol) in acetone (61.4 mL) and the mixture was stirred vigorously. Methyl bromoacetate (2.8 mL, 29 mmol) was then added and the mixture was stirred at room temperature for 3.5 hours. Upon completion of the reaction, the reaction mixture was concentrated under reduced pressure and then washed with 110 mL of water and extracted with ethyl acetate (EtOAc). The organic layer was separated, dried with anhydrous Na2SO4, filtered and concentrated to give a colorless oil which solidified to a white solid under vacuum in 82% isolated yield. The product was characterized by 1H NMR (400 MHz, CDCl3): δ 9.87 (s, 1H), 7.82 (d, J = 8.8 Hz, 2H), 6.98 (d, J = 8.7 Hz, 2H), 4.70 (s, 2H), 3.79 (s, 3H). eSI-MS (m/z): 195.1 [M + H]+.

References

[1] Organic Letters, 2011, vol. 13, # 20, p. 5656 - 5659
[2] Organic Letters, 2004, vol. 6, # 12, p. 2019 - 2022
[3] Chemistry - A European Journal, 2008, vol. 14, # 19, p. 5812 - 5819
[4] Patent: WO2015/65716, 2015, A1. Location in patent: Paragraph 00490
[5] Patent: WO2016/144958, 2016, A1. Location in patent: Paragraph 00296

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