Phenol → Phenyl phenylacetate

HRID 2292121Notes

Reaction equation

HRID 2292121 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:8]1([CH2:14][C:15](Cl)=[O:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>ClCCl.N1C=CC=CC=1>[C:8]1([CH2:14][C:15]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[O:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 996PhenolHCID 7679Phenylacetyl chloride

Product 1

HCID 164721Phenyl phenylacetateYield 95.6%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

Phenol (47.9 g) was dissolved in dichloromethane (250 ml) and pyridine (44.3 g). Phenylacetyl chloride (78.8 g) was added with stirring over 40 min., and the resulting mixture allowed to stand at room temperature for 1 hr. The mixture was washed sequentially with water, twice with dilute hydrochloric acid, once with dilute sodium hydroxide solution, and then once with saturated brine. The solution was dried and evaporated to give phenyl phenylacetate 103.3 g., m.pt 39°-41°.

Workup

  1. waitto stand at room temperature for 1 hr
  2. washThe mixture was washed sequentially with water, twice with dilute hydrochloric acid, once with dilute sodium hydroxide solution
  3. customThe solution was dried
  4. customevaporated

Sources & evidence

ORD record
ord-021f2ec649524e079520067619bd1e06
Source dataset
uspto-grants-1989_01
Patent number
US04801593

Reaction notes

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