Water → HCID 53994779, compound

HRID 264481Notes

Reaction equation

HRID 264481 reaction equation
[CH:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][CH2:9][C:10]2=[O:13])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[CH3:14][CH:15](O)[CH:16]=[CH2:17].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>COC(OC)(C)C>[CH2:14]([CH:9]1[CH2:8][C:7]2[C:11](=[CH:12][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][CH:6]=2)[C:10]1=[O:13])[CH:15]=[CH:16][CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 117163-Buten-2-olHCID 19710254HCID 19710254, compound

Product 1

HCID 53994779HCID 53994779, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 64952,2-DimethoxypropaneSolvent

Procedure

A solution of 11.2 g of 6-isopropyl-1-indanone, 13.3 ml of 3-buten-2-ol and 110 mg of p-toluenesulfonic acid in 110 ml of 2,2-dimethoxy-propane was boiled under reflux for 89 hours on a water separator filled with molecular sieve (0.4 nm, 2 mm pearl shaped). The reaction mixture was subsequently concentrated in a vacuum and purified by column chromatography on silica gel (hexane/diethyl ether 5:1). In addition to 6.6 g of educt, there were obtained 5.6 g (38%) of (RS)-2-(2-buten-1-yl)-6-isopropyl-1-indanone as a yellow oil.

Workup

  1. additionseparator filled with molecular sieve (0.4 nm, 2 mm pearl shaped)
  2. concentrationThe reaction mixture was subsequently concentrated in a vacuum
  3. custompurified by column chromatography on silica gel (hexane/diethyl ether 5:1)
  4. additionIn addition to 6.6 g of educt

Sources & evidence

ORD record
ord-07bb0f2946024d01ae736fbc116ae3f5
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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