Water → 2-Methyl-5-benzyloxy-6,7-dichloro-1-indanone

HRID 839676Notes

Reaction equation

HRID 839676 reaction equation
[CH3:1][CH:2]1[CH2:10][C:9]2[C:4](=[C:5]([Cl:13])[C:6]([Cl:12])=[C:7]([OH:11])[CH:8]=2)[C:3]1=[O:14].C(=O)([O-])[O-].[K+].[K+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O>CN(C)C=O>[CH3:1][CH:2]1[CH2:10][C:9]2[C:4](=[C:5]([Cl:13])[C:6]([Cl:12])=[C:7]([O:11][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:8]=2)[C:3]1=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 124236132-Methyl-5-hydroxy-6,7-dichloro-1-indanone

Product 1

HCID 124236142-Methyl-5-benzyloxy-6,7-dichloro-1-indanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred mixture of 2-methyl-5-hydroxy-6,7-dichloro-1-indanone (27.6 g., 0.12 mole), potassium carbonate (24.9 g., 0.18 mole) and benzyl bromide (21.4 ml., 0.18 mole) in dimethylformamide (100 ml.) is warmed at 55°-60° C. for 2 hrs., then poured into water (1 l.) to precipitate 35.5 g. of 2-methyl-5-benzyloxy-6,7-dichloro-1-indanone which melts at 153°-155° C. after crystallization from benzene:hexane, 3:2.

Workup

  1. temperatureis warmed at 55°-60° C. for 2 hrs
  2. customto precipitate 35.5 g
  3. customof 2-methyl-5-benzyloxy-6,7-dichloro-1-indanone which melts at 153°-155° C. after crystallization from benzene

Sources & evidence

ORD record
ord-08cc15ce467c4dae8cd819620b8eb37b
Source dataset
uspto-grants-1978_06
Patent number
US04096267

Reaction notes

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