Ethanol → Ethyl (4-chlorophenyl)acetate

HRID 1870779Notes

Reaction equation

HRID 1870779 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[CH2:12](O)[CH3:13]>C1(C)C=CC(S(O)(=O)=O)=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 15880(4-Chlorophenyl)acetic acid

Product 1

HCID 84177Ethyl (4-chlorophenyl)acetate

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidSolvent

Procedure

First, 17.24 g of 4-chlorophenylacetic acid was dissolved in 200 ml of ethanol, to which a catalytic amount of p-toluenesulfonic acid was added, and the mixture was heated under reflux for 10 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and concentrated. The residue was poured into water and extracted with ethyl acetate, and the organic layer was dried and then concentrated. The residue was subjected to silica gel chromatography, which afforded 19.0 g of ethyl 4-chlorophenylacetate.

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 10 hours
  4. customAfter completion of the reaction
  5. concentrationconcentrated
  6. additionThe residue was poured into water
  7. extractionextracted with ethyl acetate
  8. customthe organic layer was dried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-798996bbe3554d8bb59696b26da3d550
Source dataset
uspto-grants-2000_08
Patent number
US06100257

Reaction notes

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