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

HRID 334977Notes

Reaction equation

HRID 334977 reaction equation
[OH-].[K+].[CH2:3]([O:10][C:11]1[CH:20]=[C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:18]([C:29]([CH3:31])=[CH2:30])=[CH:17][C:12]=1[C:13]([O:15]C)=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CO.O>[CH2:3]([O:10][C:11]1[CH:20]=[C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:18]([C:29]([CH3:31])=[CH2:30])=[CH:17][C:12]=1[C:13]([OH:15])=[O:14])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=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 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Potassium hydroxide (10.96 g, 0.19 mmol) was added to a stirred suspension of methyl 2,4-bis-benzyloxy-5-isopropenyl-benzoate (61.0 g, 0.16 mol) in methanol (750 ml) and water (250 ml) and the mixture was stirred and held at reflux for 16 hours. Upon cooling the organic solvent was removed in vacuo and the mixture acidified to pH 2 or below by the addition of 2M hydrochloric acid (200 ml). The mixture was diluted with water (2 L) and extracted with ethyl acetate (2 L), the organic layer was separated and the solvent removed in vacuo to afford 2,4-bis-benzyloxy-5-isopropenyl-benzoic acid (58.8 g, 100%) 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 16 hours
  2. temperatureUpon cooling the organic solvent
  3. customwas removed in vacuo
  4. additionthe mixture acidified to pH 2 or below by the addition of 2M hydrochloric acid (200 ml)
  5. additionThe mixture was diluted with water (2 L)
  6. extractionextracted with ethyl acetate (2 L)
  7. customthe organic layer was separated
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-63c8541495c24c9b9489569e326e5d63
Source dataset
uspto-grants-2014_11
Patent number
US08883790B2

Reaction notes

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