Acetic Anhydride → 3-CHLOROPHENYL ACETATE

HRID 1078370Notes

Reaction equation

HRID 1078370 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[C:9](OC(=O)C)(=[O:11])[CH3:10]>S(=O)(=O)(O)O.O>[C:9]([O:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)(=[O:11])[CH3:10]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 79333-Chlorophenol

Product 1

HCID 830613-CHLOROPHENYL ACETATE

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 962WaterSolvent

Procedure

Concentrated sulphuric acid (5 drops) was added cautiously to a stirred mixture of 3-chlorophenol (74 g) and acetic anhydride (64.6 g) at ambient temperature. The mixture was left to stand for 18 hours and then added to water (300 ml). The mixture was extracted with dichloromethane and the combined extracts washed with sodium bicarbonate solution, dried and evaporated under reduced pressure. The oil obtained was distilled under vacuum to give 3-chlorophenyl acetate b.p. 116°-118° C. (2 mmHg).

Workup

  1. waitThe mixture was left
  2. extractionThe mixture was extracted with dichloromethane
  3. washthe combined extracts washed with sodium bicarbonate solution
  4. customdried
  5. customevaporated under reduced pressure
  6. customThe oil obtained
  7. distillationwas distilled under vacuum

Sources & evidence

ORD record
ord-2dfcfb818a634cb489dba3f963119198
Source dataset
uspto-grants-1996_08
Patent number
US05547972

Reaction notes

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