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

HRID 1650216Notes

Reaction equation

HRID 1650216 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. mp 114°-115° C. IR (CHCl3) 3300, 2950, 2930, 2855, 1695, 1595 cm-1. NMR (CDCl3, δ): 0.84 (6H, t, J=7 Hz), 0.95-1.35 (8H, m), 1.50-1.75 (4H, m), 2.93 (2H, s), 5.70 (1H, br s), 7.07 (1H, d, J=8 Hz), 7.28 (1H, t, J=8 Hz), 7.36 (1H, d, J=8 Hz).

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-cf7d8fae5ebf4c1ab0a563e90b0d94fa
Source dataset
uspto-grants-1990_05
Patent number
US04923881

Reaction notes

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