Monobenzone → HCID 86756615, compound

HRID 324157Notes

Reaction equation

HRID 324157 reaction equation
[CH3:1][C@H:2]([O:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH2:19]([O:26][C:27]1[CH:32]=[CH:31][C:30](O)=[CH:29][CH:28]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C1CCC(N=C=NC2CCCCC2)CC1>ClCCl>[CH3:1][C@H:2]([O:9][C:10]1[CH:11]=[CH:12][C:13]([C:14]([O:16][C:30]2[CH:31]=[CH:32][C:27]([O:26][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:28][CH:29]=2)=[O:15])=[CH:17][CH:18]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 7638MonobenzoneHCID 10868DicyclohexylcarbodiimideHCID 13878421HCID 13878421, compound

Product 1

HCID 86756615HCID 86756615, compoundYield 102.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

{circle around (1)}: A mixture comprising 1.25 g of (S)-4-(1′-methylheptyloxy)benzoic acid, 1.0 g of 4-benzyloxyphenol, 1.03 g of DCC and 10 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, followed by distilling off dichloromethane from the filtrate under reduced pressure. The resultant residue was purified by means of silica gel column chromatography, whereby 2.21 g of (S)-4-[4′-(1″-methylheptyloxy)phenylcarbonyloxy)-1-benzyloxybenzene was obtained.

Workup

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

Sources & evidence

ORD record
ord-488fd2cbc9084c6ab1991c2428065d83
Source dataset
uspto-grants-2001_04
Patent number
US06217793B1

Reaction notes

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