p-Toluenesulfonic acid → (RS)-2-(2-buten-1-yl)-7-methoxy-1-indanone

HRID 264560Notes

Reaction equation

HRID 264560 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[C:10](=[O:12])[CH2:9][CH2:8]2.[CH3:13][CH:14](O)[CH:15]=[CH2:16].C1(C)C=CC(S(O)(=O)=O)=CC=1>COC(OC)(C)C.C1(C)C=CC=CC=1>[CH2:13]([CH:9]1[CH2:8][C:7]2[C:11](=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][CH:6]=2)[C:10]1=[O:12])[CH:14]=[CH:15][CH3:16]

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 117163-Buten-2-olHCID 2881437-Methoxy-1-indanone

Product 1

HCID 53703468(RS)-2-(2-buten-1-yl)-7-methoxy-1-indanoneYield 28%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 64952,2-DimethoxypropaneSolvent

Procedure

A solution of 26.4 g of 7-methoxy-1-indanone, 33.6 ml of 3-buten-2-ol and 265 mg of p-toluenesulfonic acid in 33.6 ml of 2,2-dimethoxypropane and 265 ml of anhydrous toluene was boiled under reflux for 17 hours. The reaction mixture was subsequently concentrated in a vacuum and purified by column chromatography on silica gel (hexane/diethyl ether 5:1). 9.9 g (28%) of (RS)-2-(2-buten-1-yl)-7-methoxy-1-indanone were obtained as a yellow oil.

Workup

  1. temperatureunder reflux for 17 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-0beaa01f77bd48e3a9a2adab542da3a7
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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