p-Toluenesulfonic acid → (RS)-2-(2-buten-1-yl)-4-methoxy-1-indanone

HRID 264567Notes

Reaction equation

HRID 264567 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][C:7]2=[O:12].[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:6]1[CH2:5][C:4]2[C:8](=[CH:9][CH:10]=[CH:11][C:3]=2[O:2][CH3:1])[C:7]1=[O:12])[CH:14]=[CH:15][CH3:16]

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 117163-Buten-2-olHCID 45474914-methoxy-2,3-dihydro-1H-inden-1-one

Product 1

HCID 54096783(RS)-2-(2-buten-1-yl)-4-methoxy-1-indanoneYield 23%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 64952,2-DimethoxypropaneSolvent

Procedure

A solution of 21.5 g of 4-methoxy-1-indanone, 27.4 ml of 3-buten-2-ol and 210 mg of p-toluenesulfonic acid in 27.4 ml of 2,2-dimethoxypropane and 210 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/ethyl acetate 9:1). 6.42 g (23%) of (RS)-2-(2-buten-1-yl)-4-methoxy-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/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-7ae7c1997b5c4f2e989aa6b5461b0e12
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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