O-Cresol → Acetic acid, 2-methylphenyl ester

HRID 1607966Notes

Reaction equation

HRID 1607966 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].C(N(CC)CC)C.[C:12]1([CH3:19])[C:17]([OH:18])=[CH:16][CH:15]=[CH:14][CH:13]=1>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1>[C:1]([O:18][C:17]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:19])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 335O-CresolHCID 6367Acetyl chlorideHCID 8471Triethylamine

Product 1

HCID 10778Acetic acid, 2-methylphenyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Conditions

Temperature
65 °C

Procedure

First 235.5 g (3.3 moles) acetyl chloride then 282.8 g (2.8 moles) triethylamine are added dropwise to a mixture of 324 g (3 moles) o-cresol and 36.6 g (0.3 mole) 4-dimethylaminopyridine in 1 liter of toluene. The mixture is then heated for 3 h at 65° C. The resulting solid hydrochloride is separated by filtration and the organic phase is washed twice with 1 N hydrochloric acid then with water. The solution is dried and then the solvent is recovered under vacuum. The remaining oil is distilled under vacuum. It has a boiling point of 87° C. at 12 Torr. The yield is 428.8 g.

Workup

  1. customThe resulting solid hydrochloride is separated by filtration
  2. washthe organic phase is washed twice with 1 N hydrochloric acid
  3. customThe solution is dried
  4. customthe solvent is recovered under vacuum
  5. distillationThe remaining oil is distilled under vacuum

Sources & evidence

ORD record
ord-c3bb34f7e822469ba19691b32d537e52
Source dataset
uspto-grants-1989_09
Patent number
US04868256

Reaction notes

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