Benzyl 4-(4'-decyloxybenzoyloxy)benzoate → 4-(4-(Decyloxy)benzoyloxy)benzoic acid

HRID 727973Notes

Reaction equation

HRID 727973 reaction equation
[CH2:1]([O:11][C:12]1[CH:36]=[CH:35][C:15]([C:16]([O:18][C:19]2[CH:34]=[CH:33][C:22]([C:23]([O:25]CC3C=CC=CC=3)=[O:24])=[CH:21][CH:20]=2)=[O:17])=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]>C(OCC)(=O)C.[Pd]>[CH2:1]([O:11][C:12]1[CH:36]=[CH:35][C:15]([C:16]([O:18][C:19]2[CH:34]=[CH:33][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=2)=[O:17])=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

4

Reactant 1

HCID 19824466Benzyl 4-(4'-decyloxybenzoyloxy)benzoate

Product 1

HCID 158098324-(4-(Decyloxy)benzoyloxy)benzoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

In 10 ml of pyridine was dissolved 2.3 g of benzyl p-hydroxybenzoate, a solution of 3 g of p-decyloxybenzoic acid chloride in 15 ml of pyridine was added to the above solution, and a reaction was carried out at room temperature overnight. The reaction liquid was put in ice-cooled dilute hydrochloric acid and the formed precipitate was recovered by filtration, dried and purified by the silica gel chromatography to obtain 4 g of benzyl 4-(4'-decyloxybenzoyloxy)benzoate. This ester was dissolved in 20 ml of ethyl acetate and 0.4 g of Pd/C was added. Catalytic reduction was carried out under a hydrogen pressure of 2 kg/cm2 overnight. The catalyst was removed by filtration, and ethyl acetate was evaporated from the reaction liquid to obtain 3.2 g of 4-(4'-decyloxybenzoyloxy)benzoic acid.

Workup

  1. custompressure of 2 kg/cm2 overnight
  2. customThe catalyst was removed by filtration, and ethyl acetate
  3. customwas evaporated from the reaction liquid

Sources & evidence

ORD record
ord-dc418a57a1af427e8c6fd44870cecd5a
Source dataset
uspto-grants-1991_09
Patent number
US05045228

Reaction notes

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