Potassium Hydroxide → 4-(4'Heptyloxybenzyloxy)benzoic acid

HRID 727979Notes

Reaction equation

HRID 727979 reaction equation
[CH2:1]([O:8][C:9]1[CH:27]=[CH:26][C:12]([CH2:13][O:14][C:15]2[CH:25]=[CH:24][C:18]([C:19]([O:21]CC)=[O:20])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[OH-].[K+]>C(O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][O:14][C:15]2[CH:16]=[CH:17][C:18]([C:19]([OH:21])=[O:20])=[CH:24][CH:25]=2)=[CH:26][CH:27]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 19824471Ethyl 4-(4'-heptyloxybenzyloxy)benzoate

Product 1

HCID 198244724-(4'Heptyloxybenzyloxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 20 ml of benzene were dissolved 2.2 g of 4-heptyloxybenzyl alcohol and 1.7 g of ethyl 4-hydroxybenzoate, 1.8 g of diethyl azodicarboxylate and 2.6 g of triphenylphosphine were added to the solution, and a reaction was carried out with stirring. The reaction liquid was concentrated and the concentrate was separated and purified by the silica gel chromatography to obtain 3.1 g of ethyl 4-(4'-heptyloxybenzyloxy)benzoate. This ester was dissolved in 20 ml of ethanol and 4.2 ml of a 2N aqueous KOH solution was added to the solution to effect the hydrolysis. The reaction mixture was treated by customary procedures to obtain 2.7 g of 4-(4'heptyloxybenzyloxy)benzoic acid.

Workup

  1. customthe hydrolysis
  2. additionThe reaction mixture was treated by customary procedures

Sources & evidence

ORD record
ord-4d120deb8a3249a79e97478d52098b0d
Source dataset
uspto-grants-1991_09
Patent number
US05045228

Reaction notes

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