Chloroform → 2,5-Xylyl acetate

HRID 628525Notes

Reaction equation

HRID 628525 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[OH:9].C(Cl)(Cl)Cl.[C:14](Cl)(=[O:16])[CH3:15]>C(N(CC)CC)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[O:9][C:14](=[O:16])[CH3:15]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 6367Acetyl chlorideHCID 72672,5-Dimethylphenol

Product 1

HCID 701412,5-Xylyl acetateYield 89.3%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

At 0° C., to a mixture of 2,5-dimethylphenol 20 g and chloroform 150 ml was added acetyl chloride 15 g and triethylamine 49 g. The resulting mixture was raised to room temperature and was stirred for four hours. Then, the reaction mixture was extracted with chloroform. 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 acetic acid 2,5-dimethylphenyl ester 24 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-d3d17e7917bc4ec089aba6bdcf640503
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

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