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

HRID 603974Notes

Reaction equation

HRID 603974 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-6093623d7d4248f99c0ac43c7d6fc5ec
Source dataset
uspto-grants-2011_03
Patent number
US07906548B2

Reaction notes

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