Benzene → 2,2-Dibutyl-4-hydroxy-1-indanone

HRID 346224Notes

Reaction equation

HRID 346224 reaction equation
[Si]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH2:11][CH2:12][C:13]2=[O:18])(C(C)(C)C)(C)C.I[CH2:20][CH2:21][CH2:22][CH3:23].CC(C)([O-])C.[K+].O.[CH:31]1[CH:36]=CC=[CH:33][CH:32]=1>>[CH2:20]([C:12]1([CH2:36][CH2:31][CH2:32][CH3:33])[CH2:11][C:10]2[C:14](=[CH:15][CH:16]=[CH:17][C:9]=2[OH:8])[C:13]1=[O:18])[CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 5

HCID 241BenzeneHCID 962WaterHCID 10962Butyl iodideHCID 158291994-{[tert-Butyl(dimethyl)silyl]oxy}-2,3-dihydro-1H-inden-1-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 106590162,2-Dibutyl-4-hydroxy-1-indanone

Procedure

A mixture of 4-(tert-butyldimethylsilyl)oxy-1-indanone (524 mg), 1-iodobutane (0.91 ml), and potassium tert-butoxide (896 mg) in dry benzene (15 ml) was refluxed for 2 hours under nitrogen. The reaction mixture was allowed to cool and poured into water. The separated oil was extracted with ethyl acetate. The organic layer was washed with brine, and concentrated in vacuo. The residue was subjected to column-chromatography on silica gel (elution by 10% n-hexane in dichloromethane and then dichloromethane) to yield 2,2-dibutyl-4-hydroxy-1-indanone (150 mg) as crystals.

Workup

  1. temperaturewas refluxed for 2 hours under nitrogen
  2. temperatureto cool
  3. extractionThe separated oil was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. concentrationconcentrated in vacuo
  6. washelution by 10% n-hexane in dichloromethane

Sources & evidence

ORD record
ord-b34b65a860e247639f4feac56a380174
Source dataset
uspto-grants-1991_10
Patent number
US05061718

Reaction notes

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