Monobenzone → HCID 20645779, compound

HRID 324152Notes

Reaction equation

HRID 324152 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:16][C@H:17]([C:26](O)=[O:27])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].C1CCC(N=C=NC2CCCCC2)CC1>ClCCl>[CH3:16][C@H:17]([C:26]([O:15][C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:14][CH:13]=1)=[O:27])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 7638MonobenzoneHCID 10868DicyclohexylcarbodiimideHCID 11063144(S)-1-methylnonylcarboxylic acid

Product 1

HCID 20645779HCID 20645779, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

{circle around (1)}: A mixture comprising 2.00 g of 4-benzyloxyphenol, 1.86 g of (S)-1-methylnonylcarboxylic acid, 2.06 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, followed by distilling off dichloromethane from the filtrate. The resultant residue was purified by means of silica gel column chromatography, whereby 3.2 g of (S)-4-(1′-methylnonylcarbonyloxy)-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
  5. customThe resultant residue was purified by means of silica gel column chromatography

Sources & evidence

ORD record
ord-2882d96fd87c445d98ec9f07cda9d41a
Source dataset
uspto-grants-2001_04
Patent number
US06217793B1

Reaction notes

Loading…