Potassium Hydroxide → 2-Hydroxy-5-isopropyl-4-methoxybenzoic acid

HRID 389953Notes

Reaction equation

HRID 389953 reaction equation
[OH-].[K+].[OH:3][C:4]1[CH:13]=[C:12]([O:14][CH3:15])[C:11]([CH:16]([CH3:18])[CH3:17])=[CH:10][C:5]=1[C:6]([O:8]C)=[O:7]>CO.O>[OH:3][C:4]1[CH:13]=[C:12]([O:14][CH3:15])[C:11]([CH:16]([CH3:18])[CH3:17])=[CH:10][C:5]=1[C:6]([OH:8])=[O:7]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 58236455Methyl 2-hydroxy-5-isopropyl-4-methoxybenzoate

Product 1

HCID 582364542-Hydroxy-5-isopropyl-4-methoxybenzoic acidYield 70%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Aqueous potassium hydroxide (50% w/v, 0.2 ml) was added to a suspension of methyl 2-hydroxy-5-isopropyl-4-methoxybenzoate (420 mg, 1.88 mmol) in methanol (5 ml) and water (2 ml) and the mixture was stirred and held at reflux for 3 hours. Upon cooling to room temperature the organic solvent was removed in vacuo and the residue acidified by the addition of 2M hydrochloric acid (10 ml). The solid material was collected by suction filtration, rinsed with water (2×10 ml) and sucked dry under reduced pressure to afford 2-hydroxy-5-isopropyl-4-methoxybenzoic acid (275 mg, 70%) as a colourless solid. 1H NMR (DMSO-d6) 13.50 (1H, br s), 11.40 (1H, br s), 7.53 (1H, s), 6.51 (1H, s), 3.83 (3H, s), 3.12 (1H, m), 1.13 (6H, d). MS: [M+H]+ 211.

Workup

  1. temperatureat reflux for 3 hours
  2. customwas removed in vacuo
  3. additionthe residue acidified by the addition of 2M hydrochloric acid (10 ml)
  4. filtrationThe solid material was collected by suction filtration
  5. washrinsed with water (2×10 ml)
  6. customsucked dry under reduced pressure

Sources & evidence

ORD record
ord-6cdd1e6432c84486bd22850e3161b179
Source dataset
uspto-grants-2013_02
Patent number
US08383619B2

Reaction notes

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