Acetic Anhydride → HCID 58780900, compound

HRID 1373174Notes

Reaction equation

HRID 1373174 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])[CH:10]=1)[C:5]([OH:7])=[O:6].[C:20](OC(=O)C)(=[O:22])[CH3:21]>C(O)(=O)C>[C:20]([O:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])[CH:10]=1)[C:5]([OH:7])=[O:6])(=[O:22])[CH3:21]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 58780925HCID 58780925, compound

Product 1

HCID 58780900HCID 58780900, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

3-Hydroxy-5-(2-methylbenzyloxy) benzoic acid (20.30 g, 78.6 mM) and acetic anhydride (125 ml, 1.32M) in acetic acid (125 ml) were refluxed for 16 hours. The reaction was cooled and the solvent evaporated ‘in vacuo’. Acetic acid (125 nml) and water (125 ml) were added to the resulting residue and the mixture was stirred for 1 hour at 50° C. Toluene (100 ml) was added and the solvent distilled off ‘in vacuo’ to give 3-acetoxy-5-(2-methylbenzyloxy) benzoic acid as a colourless solid (23.6 g); H1 NMR δ (d6-DMSO) 2.25 (3H s) 2.32 (3H s) 5.12 (2H s) 7.09–7.25 (7H, m).

Workup

  1. temperatureThe reaction was cooled
  2. customthe solvent evaporated ‘in vacuo’
  3. additionAcetic acid (125 nml) and water (125 ml) were added to the resulting residue
  4. additionToluene (100 ml) was added
  5. distillationthe solvent distilled off ‘in vacuo’

Sources & evidence

ORD record
ord-bdb1efd5f3b14de8a0d00d011265b3f4
Source dataset
uspto-grants-2007_01
Patent number
US07160906B2

Reaction notes

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