Ethyl Acetate → 4-Acetoxymethyl-2-methoxyphenol

HRID 707634Notes

Reaction equation

HRID 707634 reaction equation
[CH2:1]([OH:11])[C:2]1[CH:10]=[CH:9][C:7]([OH:8])=[C:4]([O:5][CH3:6])[CH:3]=1.[C:12](OCC)(=[O:14])[CH3:13]>>[C:12]([O:11][CH2:1][C:2]1[CH:10]=[CH:9][C:7]([OH:8])=[C:4]([O:5][CH3:6])[CH:3]=1)(=[O:14])[CH3:13]

Participants

3

Reactant 2

HCID 8857Ethyl AcetateHCID 62348Vanillyl alcohol

Product 1

HCID 5294014-Acetoxymethyl-2-methoxyphenolYield 89%

Conditions

Temperature
65 °C

Procedure

Vanillyl alcohol (5) (10.3 g, 66.8 mmol) was dissolved in ethyl acetate (160 ml) at room temperature, Novozym 435 (2.00 g) was added, and the mixture was stirred at 65° C. for 69 hours. Then, the reaction mixture was cooled to room temperature, the enzyme was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (gradient; ethyl acetate:n-hexane=19:81→40:60) to give 4-acetoxymethyl-2-methoxyphenol (6) (11.8 g, 59.8 mmol, yield 89%) as a colorless solid.

Workup

  1. temperatureThen, the reaction mixture was cooled to room temperature
  2. filtrationthe enzyme was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (gradient; ethyl acetate:n-hexane=19:81→40:60)

Sources & evidence

ORD record
ord-5291c4b6f91b443f8f86f51a23e7bfe9
Source dataset
uspto-grants-2015_11
Patent number
US09175028B2

Reaction notes

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