Benzyl 4-n-dodecylcarbonyloxybenzoate → 4-n-Dodecylcarbonyloxybenzoic acid

HRID 324149Notes

Reaction equation

HRID 324149 reaction equation
[CH2:1]([C:13]([O:15][C:16]1[CH:31]=[CH:30][C:19]([C:20]([O:22]CC2C=CC=CC=2)=[O:21])=[CH:18][CH:17]=1)=[O:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]>[Pd].C(OCC)(=O)C>[CH2:1]([C:13]([O:15][C:16]1[CH:31]=[CH:30][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=1)=[O:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 1

HCID 22002898Benzyl 4-n-dodecylcarbonyloxybenzoate

Product 1

HCID 220028734-n-Dodecylcarbonyloxybenzoic acidYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

{circle around (2)}: A mixture comprising 3.5 g of benzyl 4-n-dodecylcarbonyloxybenzoate, 0.4 g of palladium/carbon and 20 g of ethyl acetate was stirred for 6 hours under hydrogen atmosphere. Then, palladium/carbon was filtered off, and ethyl acetate was distilled off from the filtrate. The resultant residue was recrystallized from toluene, whereby 2.40 g of 4-n-dodecylcarbonyloxybenzoic acid was obtained in the form of a colorless crystal.

Workup

  1. filtrationThen, palladium/carbon was filtered off
  2. distillationethyl acetate was distilled off from the filtrate
  3. customThe resultant residue was recrystallized from toluene

Sources & evidence

ORD record
ord-6d4cec3c86ba4e7e8177b7e1ef0d4e52
Source dataset
uspto-grants-2001_04
Patent number
US06217793B1

Reaction notes

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