4-(4'-n-Dodecylcarbonyloxyphenylcarbonyloxy)-1-benzyloxybenzene → 4-(4'-n-Dodecylcarbonyloxyphenylcarbonyloxy)phenol

HRID 324151Notes

Reaction equation

HRID 324151 reaction equation
[CH2:1]([C:13]([O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([O:24][C:25]2[CH:30]=[CH:29][C:28]([O:31]CC3C=CC=CC=3)=[CH:27][CH:26]=2)=[O:23])=[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:17]=[CH:18][C:19]([C:22]([O:24][C:25]2[CH:26]=[CH:27][C:28]([OH:31])=[CH:29][CH:30]=2)=[O:23])=[CH:20][CH:21]=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 220029464-(4'-n-Dodecylcarbonyloxyphenylcarbonyloxy)-1-benzyloxybenzene

Product 1

HCID 220028074-(4'-n-Dodecylcarbonyloxyphenylcarbonyloxy)phenolYield 91.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

{circle around (4)}: A mixture comprising 3.3 g of 4-(4′-n-dodecylcarbonyloxyphenylcarbonyloxy)-1-benzyloxybenzene, 0.3 g of palladium/carbon and 20 g of ethyl acetate was stirred for 6 hours under hydrogen atmosphere. Then, palladium/carbon was filtered off, followed by distilling off ethyl acetate from the filtrate. The resultant residue was recrystallized from toluene, whereby 2.5 g of 4-(4′-n-dodecylcarbonyloxyphenylcarbonyloxy)phenol was obtained in the form of a colorless crystal.

Workup

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

Sources & evidence

ORD record
ord-10f08b8d006147c5a61508ff7f4d0032
Source dataset
uspto-grants-2001_04
Patent number
US06217793B1

Reaction notes

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