3-Hydroxybenzoic Acid → 3-Acetoxybenzoic acid

HRID 1614282Notes

Reaction equation

HRID 1614282 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[C:11](OC(=O)C)(=[O:13])[CH3:12]>O>[C:11]([O:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6])(=[O:13])[CH3:12]

Participants

4

Reactant 2

HCID 74203-Hydroxybenzoic AcidHCID 7918Acetic Anhydride

Product 1

HCID 2386693-Acetoxybenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-hydroxybenzoic acid (24.7 grams, 0.2 mole) and acetic anhydride (40.8 grams, 0.4 mole) were mixed and heated to reflux for 3 hours. The reaction mixture was poured into water and stirred for 3 hours at room temperature. The product precipitated, was collected by filtration and recrystallized from chloroform. Yield was 21grams (58%) of white crystals. Melting point was 128°-129.5° C. Proton NMR conducted as in the preceeding preparation, but using (DMSO-d6) gave as peaks, in ppm: 2.24 (s,3H), 7.35, 7.55, 7.65, 7.8 (m, 4H), 13.2 (b, 1H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 hours
  3. customThe product precipitated
  4. filtrationwas collected by filtration
  5. customrecrystallized from chloroform
  6. customProton NMR conducted as in the preceeding preparation
  7. customgave as peaks, in ppm

Sources & evidence

ORD record
ord-48ae44457fd94b9691f172ca2e82062c
Source dataset
uspto-grants-1993_03
Patent number
US05196502

Reaction notes

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