Ethylparaben → Ethyl 4-(4'-heptyloxybenzyloxy)benzoate

HRID 727978Notes

Reaction equation

HRID 727978 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][OH:14])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].O[C:18]1[CH:28]=[CH:27][C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:20][CH:19]=1.N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][O:14][C:18]2[CH:28]=[CH:27][C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:20][CH:19]=2)=[CH:15][CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

6

Reactant 4

HCID 8434EthylparabenHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 130796974-Heptyloxybenzyl alcohol

Product 1

HCID 19824471Ethyl 4-(4'-heptyloxybenzyloxy)benzoateYield 84.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

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. additionwere added to the solution
  2. customThe reaction liquid
  3. concentrationwas concentrated
  4. customthe concentrate was separated
  5. custompurified by the silica gel chromatography

Sources & evidence

ORD record
ord-e1a7c6d219474774a7e08674551e45e8
Source dataset
uspto-grants-1991_09
Patent number
US05045228

Reaction notes

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