Benzyl Bromide → HCID 11022895, compound

HRID 367336Notes

Reaction equation

HRID 367336 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([OH:15])=[C:8]([CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH:9]=1)(=[O:3])[CH3:2].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].CCCCCC>CN(C)C=O.O>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:8]([CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH:9]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 8058HexaneHCID 11430Potassium CarbonateHCID 15499742HCID 15499742, compound

Product 1

HCID 11022895HCID 11022895, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Methyl 2-(5-acetyl-2-hydroxyphenyl)acetate (8.0 g) was dissolved in 120 ml of N,N-dimethylformamide, 5 ml of benzyl bromide and 5.8 g of potassium carbonate were added to the solution, and the mixture was stirred at room temperature for 16 hours. About 100 g of ice and 200 ml of hexane were added to the reaction solution, and the mixture was vigorously stirred while adding 200 ml of water. Thereafter, the precipitated crystals were collected by filtration and recrystallized from methylene chloride-hexane to give 10.1 g of methyl 2-(5-acetyl-2-benzyloxyphenyl)acetate having a melting point of 85 to 87° C.

Workup

  1. stirringthe mixture was vigorously stirred
  2. filtrationThereafter, the precipitated crystals were collected by filtration
  3. customrecrystallized from methylene chloride-hexane

Sources & evidence

ORD record
ord-e8fde45cd4ef4af88320cc8c494ae1d5
Source dataset
uspto-grants-2000_10
Patent number
US06133266

Reaction notes

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