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

HRID 324150Notes

Reaction equation

HRID 324150 reaction equation
[CH2:1]([C:13]([O:15][C:16]1[CH:24]=[CH:23][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].[CH2:25]([O:32][C:33]1[CH:38]=[CH:37][C:36](O)=[CH:35][CH:34]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C1CCC(N=C=NC2CCCCC2)CC1>ClCCl>[CH2:1]([C:13]([O:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([O:22][C:36]2[CH:37]=[CH:38][C:33]([O:32][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:34][CH:35]=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]

Participants

5

Reactant 3

HCID 7638MonobenzoneHCID 10868DicyclohexylcarbodiimideHCID 220028734-n-Dodecylcarbonyloxybenzoic acid

Product 1

HCID 220029464-(4'-n-Dodecylcarbonyloxyphenylcarbonyloxy)-1-benzyloxybenzeneYield 99.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

{circle around (3)}: A mixture comprising 2.14 g of 4-n-dodecylcarbonyloxybenzoic acid, 1.40 g of 4-benzyloxyphenol, 1.44 g of DCC and 20 g of dichloromethane was stirred at room temperature for 30 minutes. Then, a catalytic amount of 4-N,N-dimethylaminopyridine was added to the mixture, and the mixture was further stirred at room temperature for 12 hours. After finishing the reaction, insoluble substances were filtered off, and dichloromethane was distilled off from the filtrate under reduced pressure. The resultant residue was purified by means of silica gel column chromatography, whereby 3.3 g of 4-(4′-n-dodecylcarbonyloxyphenylcarbonyloxy)-1-benzyloxybenzene was obtained in the form of a colorless crystal.

Workup

  1. stirringthe mixture was further stirred at room temperature for 12 hours
  2. customthe reaction, insoluble substances
  3. filtrationwere filtered off
  4. distillationdichloromethane was distilled off from the filtrate under reduced pressure
  5. customThe resultant residue was purified by means of silica gel column chromatography

Sources & evidence

ORD record
ord-70e9651e25d245979617f01a2b29c2af
Source dataset
uspto-grants-2001_04
Patent number
US06217793B1

Reaction notes

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