Hydrochloric Acid → Benzyl 4-(4'-decyloxybenzoyloxy)benzoate

HRID 727972

Reaction equation

HRID 727972 reaction equation
[OH:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])=[CH:4][CH:3]=1.[CH2:18]([O:28][C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].Cl>N1C=CC=CC=1>[CH2:18]([O:28][C:29]1[CH:30]=[CH:31][C:32]([C:33]([O:1][C:2]2[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:7])=[CH:4][CH:3]=2)=[O:34])=[CH:36][CH:37]=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7180Benzyl 4-HydroxybenzoateHCID 117793534-Decyloxybenzoyl chloride

Product 1

HCID 19824466Benzyl 4-(4'-decyloxybenzoyloxy)benzoateYield 81.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

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. customThe reaction liquid
  2. filtrationthe formed precipitate was recovered by filtration
  3. customdried
  4. custompurified by the silica gel chromatography

Sources & evidence

ORD record
ord-8565aa374882420b8a5ad08164479cd9
Source dataset
uspto-grants-1991_09
Patent number
US05045228

Linked notes

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