Water → HCID 53950047, compound

HRID 264384Notes

Reaction equation

HRID 264384 reaction equation
[CH2:1]([C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH3:14])([CH3:13])[CH2:8][C:9]2=[O:12])=[CH:5][CH:4]=1)[CH3:2].[CH3:15][CH:16](O)[CH:17]=[CH2:18].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>COC(OC)(C)C>[CH2:15]([CH:8]1[C:7]([CH3:13])([CH3:14])[C:6]2[C:10](=[CH:11][C:3]([CH2:1][CH3:2])=[CH:4][CH:5]=2)[C:9]1=[O:12])[CH:16]=[CH:17][CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 117163-Buten-2-olHCID 19036359HCID 19036359, compound

Product 1

HCID 53950047HCID 53950047, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 64952,2-DimethoxypropaneSolvent

Procedure

A solution of 9.1 g of 6-ethyl-3,3-dimethyl-1-indanone, 9.98 ml of 3-buten-2-ol and 250 mg of p-toluenesulfonic acid in 100 ml of 2,2-dimethoxypropane was boiled under reflux for 88 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 6:1). In addition to 2.0 g of educt, there were obtained 8.2 g (70%) of (RS)-2-(2-buten-1-yl)-6-ethyl-3,3-dimethyl-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 6:1)
  4. additionIn addition to 2.0 g of educt

Sources & evidence

ORD record
ord-44c4faeb4ee1498885c118eddf284286
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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