1-(3,5-Di-t-butylphenyl)butan-1-ol → 1-(3,5-Di-t-butylphenyl)butan-1-one

HRID 2287451Notes

Reaction equation

HRID 2287451 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:15]([OH:19])[CH2:16][CH2:17][CH3:18])[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]>C(Cl)Cl.O=[Mn]=O>[C:1]([C:5]1[CH:6]=[C:7]([C:15](=[O:19])[CH2:16][CH2:17][CH3:18])[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 187050951-(3,5-Di-t-butylphenyl)butan-1-ol

Product 1

HCID 187050871-(3,5-Di-t-butylphenyl)butan-1-oneYield 40%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To 2.37 g (9.05 mmol) of alcohol 19 in 18 mL of CH2Cl2 was added 7.86 g (90.45 mmol) of MnO2. The reaction mixture was stirred for 3 h, then filtered (celite over silica gel pad) and the pad was washed repeatedly with 20 mL aliquots of CH2Cl2. After concentration, ketone 20 was purified by chromatography (SiO2, 3% EtOAc-hexanes) to give 941 mg (3.62 mmol) of 20 (40% yield): TLC (10% EtOAc-90% hexanes) Rf 0.7; 1H-NMR (CDCl3)δ 1.01 (t, 3H, CH2CH3), 1.34 (s, 18H, 6(CH3)), 1.78 (m, 2H, CH2CH3), 2.96 (t, J=7 Hz, 2H, CH2CH2CH3), 7.63 (t, J=1 Hz, 1H, Ar--H), 7.83 (d, J=1 Hz, 2H, Ar--H).

Workup

  1. filtrationfiltered (celite over silica gel pad)
  2. washthe pad was washed repeatedly with 20 mL aliquots of CH2Cl2
  3. concentrationAfter concentration, ketone 20
  4. customwas purified by chromatography (SiO2, 3% EtOAc-hexanes)

Sources & evidence

ORD record
ord-4d5e393dd29b4c6caa0298b471983e64
Source dataset
uspto-grants-2000_07
Patent number
US06083977

Reaction notes

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