Thionyl Chloride → (3-Acetyloxy-5-carbonochloridoylphenyl) acetate

HRID 259188

Reaction equation

HRID 259188 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([O:14][C:15](=[O:17])[CH3:16])[CH:13]=1)[C:8](O)=[O:9])(=[O:3])[CH3:2].S(Cl)([Cl:20])=O>C1C=CC=CC=1>[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([O:14][C:15](=[O:17])[CH3:16])[CH:13]=1)[C:8]([Cl:20])=[O:9])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 5398693,5-Diacetoxybenzoic Acid

Product 1

HCID 11368883(3-Acetyloxy-5-carbonochloridoylphenyl) acetateYield 83%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A stirring mixture of 68.2 g (0.29 mole) of 3,5-diacetoxybenzoic acid and 21 ml (0.29 mole) of thionyl chloride in 150 ml of dry benzene was heated in an oil bath at 80°-90° C. for 2 hours. After cooling the benzene was removed in vacuo to leave 3,5-diacetoxybenzoyl chloride as a tan, solid which was recrystallized from cyclohexane as colorless crystals, mp 87°-89° C., 61.8 g (83% yield).

Workup

  1. temperaturewas heated in an oil bath at 80°-90° C. for 2 hours
  2. customwas removed in vacuo

Sources & evidence

ORD record
ord-8d18185f9e78458cb24ec2c6cfdb123c
Source dataset
uspto-grants-1977_07
Patent number
US04036857

Linked notes

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