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

HRID 264434

Reaction equation

HRID 264434 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][C:9]2=[O:12])=[CH:5][CH:4]=1.[CH3:13][CH:14](O)[CH:15]=[CH2:16].COC(OC)(C)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:13]([CH:8]1[CH2:7][C:6]2[C:10](=[CH:11][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:9]1=[O:12])[CH:14]=[CH:15][CH3:16]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 117163-Buten-2-olHCID 3340366-Methoxy-1-Indanone

Product 1

HCID 54031441(RS)-2-(2-buten-1-yl)-6-methoxy-1-indanoneYield 55%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 20.0 g of 6-methoxy-1-indanone, 31.3 ml of 3-buten-2-ol, 53.5 ml of 2,2-dimethoxypropane and 200 mg of p-toluenesulfonic acid in 200 ml of toluene was brought to boiling. The resulting methanol/acetone mixture was distilled off and the reaction solution was subsequently boiled under reflux overnight. After cooling, the solution was washed with 50 ml of saturated sodium hydrogen carbonate solution. The aqueous washing was extracted with 50 ml of ethyl acetate, the organic phases were combined, dried with magnesium sulfate and evaporated in a vacuum. Purification on silica gel (hexane/diethyl ether 5:1) yielded 13.6 g (55%) of (RS)-2-(2-buten-1-yl)-6-methoxy-1-indanone as a pale yellow oil.

Workup

  1. distillationThe resulting methanol/acetone mixture was distilled off
  2. temperatureunder reflux overnight
  3. temperatureAfter cooling
  4. washthe solution was washed with 50 ml of saturated sodium hydrogen carbonate solution
  5. washThe aqueous washing
  6. extractionwas extracted with 50 ml of ethyl acetate
  7. dry with materialdried with magnesium sulfate
  8. customevaporated in a vacuum
  9. customPurification on silica gel (hexane/diethyl ether 5:1)

Sources & evidence

ORD record
ord-e1496153e2bd4337af31d50f11c970cb
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Linked notes

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