Potassium Hydroxide → 2-Hydroxy-5-isopropyl-4-(methoxymethyloxy)benzoic acid

HRID 1182809Notes

Reaction equation

HRID 1182809 reaction equation
[OH-].[K+].[OH:3][C:4]1[CH:13]=[C:12]([O:14][CH2:15][O:16][CH3:17])[C:11]([CH:18]([CH3:20])[CH3:19])=[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][CH2:15][O:16][CH3:17])[C:11]([CH:18]([CH3:20])[CH3:19])=[CH:10][C:5]=1[C:6]([OH:8])=[O:7]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 58236463Methyl 2-hydroxy-5-isopropyl-4-(methoxymethyloxy)benzoate

Product 1

HCID 582364622-Hydroxy-5-isopropyl-4-(methoxymethyloxy)benzoic acidYield 83.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Aqueous potassium hydroxide (50% w/v, 1 ml) was added to a mixture of methyl 2-hydroxy-5-isopropyl-4-(methoxymethyloxy)benzoate (508 mg, 2.0 mmol) in methanol (10 ml) and water (4 ml) and the mixture was stirred and held at reflux for 6 hours. Upon cooling to room temperature the organic solvent was removed in vacuo and the residue acidified by the addition of 2M hydrochloric acid (30 ml). The solid material was collected by suction filtration, rinsed with water (2×20 ml) and sucked dry under reduced pressure to afford 2-hydroxy-5-isopropyl-4-(methoxymethyloxy)benzoic acid (400 mg, 83%) as a colourless solid. 1H NMR (DMSO-d6) 13.60 (1H, br s), 11.30 (1H, br s), 7.58 (1H, s), 6.58 (1H, s), 5.30 (2H, s), 3.42 (3H, s), 3.15 (1H, m), 1.18 (6H, d). MS: [M+H]+ 241.

Workup

  1. temperatureat reflux for 6 hours
  2. customwas removed in vacuo
  3. additionthe residue acidified by the addition of 2M hydrochloric acid (30 ml)
  4. filtrationThe solid material was collected by suction filtration
  5. washrinsed with water (2×20 ml)
  6. customsucked dry under reduced pressure

Sources & evidence

ORD record
ord-7a947698db4e46b694d526d81859e60d
Source dataset
uspto-grants-2014_03
Patent number
US08664218B2

Reaction notes

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