Potassium Hydroxide → 2,4-Bis(benzyloxy)-5-isopropenylbenzoic acid

HRID 334880Notes

Reaction equation

HRID 334880 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:16]([C:27]([CH3:29])=[CH2:28])=[CH:15][C:10]=1[C:11]([O:13]C)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>CO.O>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:16]([C:27]([CH3:29])=[CH2:28])=[CH:15][C:10]=1[C:11]([OH:13])=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 11955870Methyl 2,4-bis-benzyloxy-5-isopropenylbenzoate

Product 1

HCID 498640162,4-Bis(benzyloxy)-5-isopropenylbenzoic acidYield 89%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl 2,4-bis-benzyloxy-5-isopropenyl-benzoate (700 mg, 1.80 mmol) was dissolved in methanol (20 ml), a solution of potassium hydroxide (286 mg, 5.1 mmol) in water (4 ml) was added and the mixture was stirred and held at reflux for 3 hours. Upon cooling the solvent was removed in vacuo and the mixture acidified to pH 2 or below by the addition of 2M hydrochloric acid. The mixture was extracted with dichloromethane, the organic layer was separated and the solvent removed in vacuo to afford 2,4-bis-benzyloxy-5-isopropenyl-benzoic acid (600 mg, 89%) as a colourless solid. 1H NMR (DMSO-d6) 7.52 (2H, d), 7.47-7.29 (9H, m), 6.82 (1H, s), 5.20 (2H, s), 5.17 (2H, s), 5.06 (1H, s), 5.04 (1H, s), 2.03 (3H, s). MS: [M+H]+ 375.

Workup

  1. temperatureat reflux for 3 hours
  2. temperatureUpon cooling the solvent
  3. customwas removed in vacuo
  4. additionthe mixture acidified to pH 2 or below by the addition of 2M hydrochloric acid
  5. extractionThe mixture was extracted with dichloromethane
  6. customthe organic layer was separated
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-0b28710907b24fa59eea7bec6074c4cc
Source dataset
uspto-grants-2014_11
Patent number
US08883790B2

Reaction notes

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