Methanol → 4-Hydroxy-5-isopropyl-2-methoxybenzoic acid

HRID 1182793Notes

Reaction equation

HRID 1182793 reaction equation
[OH-].[K+].[OH:3][C:4]1[CH:13]=[C:12]([O:14]C)[C:11]([CH:16]([CH3:18])[CH3:17])=[CH:10][C:5]=1[C:6]([O:8]C)=[O:7].[CH3:19]O>O>[OH:14][C:12]1[C:11]([CH:16]([CH3:18])[CH3:17])=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:3][CH3:19])[CH:13]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 58236455Methyl 2-hydroxy-5-isopropyl-4-methoxybenzoate

Product 1

HCID 582364604-Hydroxy-5-isopropyl-2-methoxybenzoic acidYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Aqueous potassium hydroxide (50% w/v, 0.5 ml) was added to a suspension of methyl 2-hydroxy-5-isopropyl-4-methoxybenzoate (418 mg, 1.87 mmol) in methanol (4 ml) and water (2 ml) and the mixture was stirred and held at reflux for 4 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 4-hydroxy-5-isopropyl-2-methoxybenzoic acid (332 mg, 85%) as an off-white solid. 1H NMR (DMSO-d6) 11.88 (1H, br s), 10.11 (1H, s), 7.54 (1H, s), 6.51 (1H, s), 3.75 (3H, s), 3.11 (1H, m), 1.13 (6H, d). MS: [M+Na]+ 233.

Workup

  1. temperatureat reflux for 4 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-0d6ed78f7d3049f7be4e70c9d95f4ddf
Source dataset
uspto-grants-2014_03
Patent number
US08664218B2

Reaction notes

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