Acetic Anhydride → Methyl 2-acetoxy-4-methylbenzoate

HRID 1739463Notes

Reaction equation

HRID 1739463 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:13](OC(=O)C)(=[O:15])[CH3:14]>N1C=CC=CC=1>[C:13]([O:1][C:2]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])(=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 78400Benzoic acid, 2-hydroxy-4-methyl-, methyl ester

Product 1

HCID 21841044Methyl 2-acetoxy-4-methylbenzoate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of methyl 2-hydroxy-4-methylbenzoate (19.7 g, 0.119 mole) in pyridine (15 ml) was treated with acetic anhydride (15 ml, 16.23 g, 0.158 mol). The reaction was stirred at ambient temperature overnight and then the solvent evaporated. The residue was dissolved in CH2Cl2 and the solution washed with 2N aqueous HCl, water, saturated aqueous NaHCO3 solution, dried (MgSO4) and evaporated to give methyl 2-acetoxy-4-methylbenzoate which was used without further purification (24.58 g, 99%).

Workup

  1. customthe solvent evaporated
  2. dissolutionThe residue was dissolved in CH2Cl2
  3. washthe solution washed with 2N aqueous HCl, water, saturated aqueous NaHCO3 solution
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-f8e20e40a51746899722a32da2e41dba
Source dataset
uspto-grants-1999_10
Patent number
US05965741

Reaction notes

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