p-Toluenesulfonic acid → HCID 53997718, compound

HRID 264556Notes

Reaction equation

HRID 264556 reaction equation
[C:1]1(=[O:10])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[CH3:11][CH:12](O)[CH:13]=[CH2:14].COC(OC)(C)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:11]([CH:2]1[CH2:3][C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:1]1=[O:10])[CH:12]=[CH:13][CH3:14]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 67351-IndanoneHCID 117163-Buten-2-ol

Product 1

HCID 53997718HCID 53997718, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 29.5 g of 1-indanone, 73.5 ml 3-buten-2-ol, 77.0 ml of 2,2-dimethoxypropane and 400 mg of p-toluenesulfonic acid in 400 ml of toluene was boiled under reflux for 24 hours. After cooling, the solution was washed with 100 ml of saturated sodium hydrogen carbonate solution. The aqueous washing was extracted with 150 ml of ethyl acetate and the organic phases were combined, dried with magnesium sulfate and evaporated in a vacuum. Purification on silica gel (hexane/diethyl ether 7:1) yielded 19.8 g (48%) of (RS)-2-(2-buten-1-yl)-1-indanone as a pale yellow oil.

Workup

  1. temperatureunder reflux for 24 hours
  2. temperatureAfter cooling
  3. washthe solution was washed with 100 ml of saturated sodium hydrogen carbonate solution
  4. washThe aqueous washing
  5. extractionwas extracted with 150 ml of ethyl acetate
  6. dry with materialdried with magnesium sulfate
  7. customevaporated in a vacuum
  8. customPurification on silica gel (hexane/diethyl ether 7:1)

Sources & evidence

ORD record
ord-431eb57ad5354f92a2636f50f2c754ed
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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