O-Cresol → 2-Methylphenyl propanoate

HRID 628549Notes

Reaction equation

HRID 628549 reaction equation
[C:1]1([CH3:8])[C:6]([OH:7])=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(Cl)Cl.[C:13](Cl)(=[O:16])[CH2:14][CH3:15]>C(N(CC)CC)C>[C:1]1([CH3:8])[CH:2]=[CH:3][CH:4]=[CH:5][C:6]=1[O:7][C:13](=[O:16])[CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 335O-CresolHCID 6212ChloroformHCID 62324Propionyl chloride

Product 1

HCID 2214362-Methylphenyl propanoateYield 92.2%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

At 0° C., to a mixture of o-cresol 10 g and chloroform 100 ml was added propionyl chloride 10 g and triethylamine 28 g. The resulting mixture was raised to room temperature and was stirred for two hours. Then the reaction mixture was extracted with chloroform and the organic layer was washed with water and was dried over anhydrous magnesium sulfate, and was then concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to give propionic acid o-tolyl ester 14 g.

Workup

  1. extractionThen the reaction mixture was extracted with chloroform
  2. washthe organic layer was washed with water
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. concentrationwas then concentrated under reduced pressure

Sources & evidence

ORD record
ord-54a01959e25d4e1fa1e1f1e50e893582
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

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