p-Toluenesulfonic acid → (RS)-2-(2-buten-1-yl)-6-chloro-1-indanone

HRID 264373

Reaction equation

HRID 264373 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.[CH3:12][CH:13](O)[CH:14]=[CH2:15].C1(C)C=CC(S(O)(=O)=O)=CC=1>COC(OC)(C)C.C1(C)C=CC=CC=1>[CH2:12]([CH:7]1[CH2:6][C:5]2[C:9](=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:8]1=[O:11])[CH:13]=[CH:14][CH3:15]

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 117163-Buten-2-olHCID 51007056-Chloro-1-indanone

Product 1

HCID 54260426(RS)-2-(2-buten-1-yl)-6-chloro-1-indanoneYield 39%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 64952,2-DimethoxypropaneSolvent

Procedure

A solution of 20.2 g of 6-chloro-1-indanone, 25 ml of 3-buten-2-ol and 200 mg of p-toluenesulfonic acid in 25 ml of 2,2-dimethoxypropane and 200 ml of anhydrous toluene was boiled under reflux for 16 hours. The reaction mixture was subsequently concentrated in a vacuum and purified by column chromatography on silica gel (hexane/diethyl ether 5:1). 10.3 g (39%) of (RS)-2-(2-buten-1-yl)-6-chloro-1-indanone were obtained as a yellow oil.

Workup

  1. temperatureunder reflux for 16 hours
  2. concentrationThe reaction mixture was subsequently concentrated in a vacuum
  3. custompurified by column chromatography on silica gel (hexane/diethyl ether 5:1)

Sources & evidence

ORD record
ord-5f8c9b4d66fb4219af2fa3d5e6bc72aa
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Linked notes

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