Acetic Anhydride → methyl (4-acetoxyphenyl)acetate

HRID 1919789Notes

Reaction equation

HRID 1919789 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH3:7][O:8][C:9](=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1.[C:19](OC(=O)C)(=[O:21])[CH3:20]>C1COCC1>[CH3:7][O:8][C:9](=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:19](=[O:21])[CH3:20])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl ester

Product 1

HCID 572417methyl (4-acetoxyphenyl)acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
44 °C

Procedure

41.5 g of K2CO3 are added to a solution of 40 g of methyl(4-hydroxyphenyl)acetate in 800 mL of anhydrous THF in a 2 L flask equipped with a magnetic stirrer, under nitrogen. 27 mL of acetic anhydride are then added at 9° C. After 1 hour of stirring at 44° C., the insoluble matter is filtered. It is washed with THF and the filtrate is concentrated to yield 53 g of expected product (white solid). The crude product is used directly for preparing the corresponding intermediate VII.

Workup

  1. customequipped with a magnetic stirrer, under nitrogen
  2. filtrationthe insoluble matter is filtered
  3. washIt is washed with THF
  4. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-4bf7a707f93346e4a26f269617a875b9
Source dataset
uspto-grants-2012_05
Patent number
US08168667B2

Reaction notes

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