Benzyl Bromide → HCID 11022895, compound

HRID 369366Notes

Reaction equation

HRID 369366 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 N,N-dimethylformamide (120 ml), and benzyl bromide (5 ml) and potassium carbonate (5.8 g) were added to the solution, then the resulting mixture was stirred for 16 hours at room temperature. Ice (ca. 100 g) and hexane (200 ml) were added to the reaction mixture, and water (200 ml) was added to the resulting mixture with vigorously stirring. The precipitated crystal was collected by filtration and recrystallized from dichloromethane-hexane to give methyl 2-(5-acetyl-2-benzyloxyphenyl)acetate (10.1 g) having a melting point of 85-87° C.

Workup

  1. additionwas added to the resulting mixture
  2. stirringwith vigorously stirring
  3. filtrationThe precipitated crystal was collected by filtration
  4. customrecrystallized from dichloromethane-hexane

Sources & evidence

ORD record
ord-f2e33c52db7e4d6894e15a95e5391e9b
Source dataset
uspto-grants-2000_10
Patent number
US06136852

Reaction notes

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