Water → Methyl 5-acetyl-2,4-dihydroxybenzoate

HRID 2355674Notes

Reaction equation

HRID 2355674 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[OH:8][C:9]1[CH:18]=[C:17]([OH:19])[CH:16]=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12].O>B(F)(F)F.CCOCC>[C:1]([C:16]1[C:17]([OH:19])=[CH:18][C:9]([OH:8])=[C:10]([CH:15]=1)[C:11]([O:13][CH3:14])=[O:12])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 16523Methyl 2,4-Dihydroxybenzoate

Product 1

HCID 12482079Methyl 5-acetyl-2,4-dihydroxybenzoateYield 42%

Reagents, catalysts & solvents 1

HCID 8000Boron trifluoride etherateSolvent

Procedure

Acetic anhydride (3.06 g, 30.0 mmol) was added to methyl 2,4-dihydroxybenzoate (5.04 g, 30.0 mmol) in boron trifluoride diethyl etherate (7.6 ml) and the mixture was stirred and held at reflux for 3 hours and then allowed to cool to room temperature. Water (80 ml) was added and the mixture stirred at room temperature for 30 minutes. The resulting yellow solid was removed by filtration and sucked as dry as possible under vacuum. The solid was dissolved in dichloromethane and washed with water, the organic layer was separated and the solvent removed in vacuo to afford methyl 5-acetyl-2,4-dihydroxybenzoate as a bright yellow solid (2.62 g, 42%) which was used without further purification. 1H NMR (DMSO-d6) 12.58 (1H, s), 11.22 (1H, s), 8.33 (1H, s), 6.45 (1H, s), 3.90 (3H, s), 2.62 (3H, s). MS: [M+H]+ 211.

Workup

  1. temperatureat reflux for 3 hours
  2. stirringthe mixture stirred at room temperature for 30 minutes
  3. customThe resulting yellow solid was removed by filtration
  4. customas dry as possible under vacuum
  5. dissolutionThe solid was dissolved in dichloromethane
  6. washwashed with water
  7. customthe organic layer was separated
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-9e97e649d5f7467aa1c8987c59dfc298
Source dataset
uspto-grants-2010_07
Patent number
US07754725B2

Reaction notes

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