4-Hydroxybenzoic Acid → Benzoic acid, 4-(acetyloxy)-

HRID 26719

Reaction equation

HRID 26719 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[C:11](Cl)(=[O:13])[CH3:12]>C1C=CC=CC=1>[C:11]([O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)(=[O:13])[CH3:12]

Participants

4

Reactant 2

HCID 1354-Hydroxybenzoic AcidHCID 6367Acetyl chloride

Product 1

HCID 16865Benzoic acid, 4-(acetyloxy)-

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 20 g. of 4-hydroxybenzoic acid in 200 ml. of benzene and 40 ml. of acetyl chloride is refluxed for 3 hours. Solvent and excess acetyl chloride are evaporated. The mixture is dissolved in methanol (150 ml.) and water (20 ml.) added; after 15 minutes, addition of more water results in the precipitation of 4-acetoxy benzoic acid, m.p. 192°-193° C.

Workup

  1. customSolvent and excess acetyl chloride are evaporated
  2. dissolutionThe mixture is dissolved in methanol (150 ml.)
  3. additionwater (20 ml.) added
  4. additionaddition of more water

Sources & evidence

ORD record
ord-97e6103d3157480888b34d018a955edc
Source dataset
uspto-grants-1979_04
Patent number
US04151297

Linked notes

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