Acetone → 1-Bromo-4-phenylmethoxybenzene

HRID 728518Notes

Reaction equation

HRID 728518 reaction equation
CC(C)=O.[CH2:5](Cl)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Br:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>O>[CH2:5]([O:20][C:17]1[CH:18]=[CH:19][C:14]([Br:13])=[CH:15][CH:16]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 7503Benzyl ChlorideHCID 78084-BromophenolHCID 11430Potassium Carbonate

Product 1

HCID 1388351-Bromo-4-phenylmethoxybenzeneYield 73%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 200 ml of acetone were added 63.5 g of benzyl chloride, 95.15 g of 4-bromophenol, and 69.1 g of potassium carbonate, and the mixture was allowed to react at reflux for 8 hours. After completion of the reaction, the reaction mixture was added into 200 ml of water and extracted with 200 ml of chloroform. The extract was washed with 200 ml of water to obtain a crude product. The crude product was distilled by a Claisen flask to obtain 108.1 g of a distillate, which was further purified by silica gel column chromatography using benzene as an eluent to give 96 g (theoretical yield: 73%) of the entitled compound having a melting point of 47° C.

Workup

  1. customto react
  2. temperatureat reflux for 8 hours
  3. customAfter completion of the reaction
  4. extractionextracted with 200 ml of chloroform
  5. washThe extract was washed with 200 ml of water

Sources & evidence

ORD record
ord-16ed070e18ef4dc885ffbdcf171d339c
Source dataset
uspto-grants-1991_09
Patent number
US05049308

Reaction notes

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