4-ACETYL-2-METHOXYPHENYL ACETATE Chemical Properties

Melting point:

54-57 °C(lit.)

Boiling point:

294.7±25.0 °C(Predicted)

Density 

1.140±0.06 g/cm3(Predicted)

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

Appearance

yellow solid

Safety Information

WGK Germany 

3

MSDS

• Language:English Provider:SigmaAldrich

4-ACETYL-2-METHOXYPHENYL ACETATE Usage And Synthesis

Definition

ChEBI: 4-acetyl-2-methoxyphenyl acetate is an acetate ester that is phenylacetate substituted by an acetyl group at position 4 and a methoxy group at position 2 respectively. It is a member of acetophenones, a monomethoxybenzene and a member of phenyl acetates.

Synthesis

General procedure for the synthesis of 1-(4-acetoxy-3-methoxyphenyl)ethanone from glacial acetic acid and vanillylacetophenone: reference to Example 1. Preparation of intermediate (1): 4-acetyl-2-methoxyphenyl acetate (1). 500 mg (3 mM) of acetylisopropyl ketone was dissolved in 20 mL of THF and 0.5 mL of pyridine and 0.6 mL of anhydrous acetic acid were added. The reaction mixture was stirred at room temperature for 3 hours. After completion of the reaction, the product was extracted with diethyl ether and the organic phase was dried with anhydrous magnesium sulfate and concentrated under reduced pressure to remove the solvent. The crude product was purified by silica gel column chromatography with hexane:ethyl acetate (4:1) as mobile phase to give 4-acetyl-2-methoxyphenyl acetate (1; 625 mg) as white solid. Melting point: 58.7 °C; 1H NMR (CDCl3): δ 7.60 (d, 1H, J = 1.8 Hz, H-3), 7.55 (dd, 1H, J = 1.8, 8.2 Hz, H-5), 7.12 (d, 1H, J = 8.2 Hz, H-6), 3.89 (s, 3H, OCH3), 2.59 (s, 3H, OCOCH3) and 2.33 (s, 3H, COCH3).

References

[1] Patent: WO2008/41826, 2008, A1. Location in patent: Page/Page column 17; 35-36

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