Water → 2-Cyclopentyl-2-methyl-5-methoxy-6,7-dichloro-1-indanone

HRID 2083460Notes

Reaction equation

HRID 2083460 reaction equation
[CH3:1][CH:2]1[CH2:10][C:9]2[C:4](=[C:5]([Cl:14])[C:6]([Cl:13])=[C:7]([O:11][CH3:12])[CH:8]=2)[C:3]1=[O:15].CC(C)([O-])C.[K+].[CH:22]1(Br)[CH2:26][CH2:25][CH2:24][CH2:23]1.O>C(O)(C)(C)C>[CH:22]1([C:2]2([CH3:1])[CH2:10][C:9]3[C:4](=[C:5]([Cl:14])[C:6]([Cl:13])=[C:7]([O:11][CH3:12])[CH:8]=3)[C:3]2=[O:15])[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

6

Reactant 4

HCID 962WaterHCID 8728BromocyclopentaneHCID 123955612-Methyl-5-methoxy-6,7-dichloro-1-indanoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 123955682-Cyclopentyl-2-methyl-5-methoxy-6,7-dichloro-1-indanone

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A solution of 2-methyl-5-methoxy-6,7-dichloro-1-indanone (7.35 g., 0.03 mole) in tert.-butyl alcohol (100 ml.) is refluxed in an inert atmosphere and treated with potassium tert.-butoxide (4.48 G., 0.04 mole). After one-half hour at reflux cyclopentyl bromide (9.9 g., 0.06 mole) is added and refluxing is continued for 1 hour. The reaction is poured into water (1 l.) affording 2-cyclopentyl-2-methyl-5-methoxy-6,7-dichloro-1-indanone which melts at 109°-111° C.

Workup

  1. additionis added
  2. temperaturerefluxing

Sources & evidence

ORD record
ord-66b0ca0719ee489e81dd0729b183377b
Source dataset
uspto-grants-1978_04
Patent number
US04085219

Reaction notes

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