Potassium Hydroxide → 2-Allyloxy-4-hydroxy-5-isopropylbenzoic acid

HRID 1182801Notes

Reaction equation

HRID 1182801 reaction equation
[OH-].[K+].[CH2:3]([O:6][C:7]1[CH:16]=[C:15]([OH:17])[C:14]([CH:18]([CH3:20])[CH3:19])=[CH:13][C:8]=1[C:9]([O:11]C)=[O:10])[CH:4]=[CH2:5]>CO.O>[CH2:3]([O:6][C:7]1[CH:16]=[C:15]([OH:17])[C:14]([CH:18]([CH3:20])[CH3:19])=[CH:13][C:8]=1[C:9]([OH:11])=[O:10])[CH:4]=[CH2:5]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 58236453Methyl 2-allyloxy-4-hydroxy-5-isopropylbenzoate

Product 1

HCID 582364562-Allyloxy-4-hydroxy-5-isopropylbenzoic acidYield 88%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Aqueous potassium hydroxide (50% w/v, 2 ml) was added to a mixture of methyl 2-allyloxy-4-hydroxy-5-isopropylbenzoate (860 mg, 3.44 mmol) in methanol (12 ml) and water (4 ml) and the mixture was stirred and held at reflux for 5 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-allyloxy-4-hydroxy-5-isopropylbenzoic acid (715 mg, 88%) as a pale green solid. 1H NMR (DMSO-d6) 11.92 (1H, br s), 10.08 (1H, s), 7.56 (1H, s), 6.48 (1H, s), 6.03 (1H, m), 5.50 (1H, dm), 5.27 (1H, dm), 4.53 (2H, m), 3.11 (1H, m), 1.13 (6H, d). MS: [M+Na]+259.

Workup

  1. temperatureat reflux for 5 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-d65fd23031c240539944cc18fbda02f4
Source dataset
uspto-grants-2014_03
Patent number
US08664218B2

Reaction notes

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