Hydrochloric Acid → Methyl 3-acetylbenzoate

HRID 615497Notes

Reaction equation

HRID 615497 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=[O:8])(=[O:3])[CH3:2].Cl.[CH3:14]O>>[C:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([O:9][CH3:14])=[O:8])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 2203243-Acetylbenzoic acid

Product 1

HCID 15094405Methyl 3-acetylbenzoate

Procedure

A solution of 5 g of 3-acetylbenzoic acid in dry MeOH was saturated with hydrogen chloride gas. The reaction vessel was stoppered and kept at room temperature for 2 days. The MeOH was evaporated and the residue extracted into diethylether and clarified by filtration. The ether was evaporated and the dark oil was chromatographed through a short column of silica gel eluting with methylene chloride. The combined fractions were evaporated to dryness giving 4.25 g of a yellow oil that solidified on standing. The solid ester was used as obtained.

Workup

  1. customThe MeOH was evaporated
  2. extractionthe residue extracted into diethylether
  3. filtrationclarified by filtration
  4. customThe ether was evaporated
  5. customthe dark oil was chromatographed through a short column of silica gel eluting with methylene chloride
  6. customThe combined fractions were evaporated to dryness

Sources & evidence

ORD record
ord-2a55d678a4c84c3cb89e75fb0aae551e
Source dataset
uspto-grants-1985_02
Patent number
US04499299

Reaction notes

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