Acetic Anhydride → 4-Acetoxy-2-hydroxy-benzoic acid methyl ester

HRID 1821521Notes

Reaction equation

HRID 1821521 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:5]=1[OH:11].CCN(CC)CC.[CH3:20][C:21](OC(C)=O)=[O:22]>CCOCC.CN(C1C=CN=CC=1)C>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:21](=[O:22])[CH3:20])=[CH:6][C:5]=1[OH:11]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 16523Methyl 2,4-Dihydroxybenzoate

Product 1

HCID 579902174-Acetoxy-2-hydroxy-benzoic acid methyl esterYield 23.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolvent

Procedure

2,4-Dihydroxy-benzoic acid methyl ester (11.76 g, 70 mmol) was dissolved in Et2O (175 mL). Then Et3N (10.78 mL, 77 mmol), Ac2O (7.28 mL, 77 mmol), and DMAP (catalytic amount) were added. The reaction solution was then stirred for one hour at room temperature. Then the reaction solution was concentrated by rotary evaporation and the resulting residue was purified with a silica gel column and dichloromethane as eluent. Obtained 3.44 g 4-Acetoxy-2-hydroxy-benzoic acid methyl ester in 23% yield.

Workup

  1. concentrationThen the reaction solution was concentrated by rotary evaporation
  2. customthe resulting residue was purified with a silica gel column and dichloromethane as eluent

Sources & evidence

ORD record
ord-9cdc2b4e1e464820bc9eaeea88b61df9
Source dataset
uspto-grants-2009_10
Patent number
US07605156B2

Reaction notes

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