6,10-Dimethyl-4-hydroxy-2,5,9-undecatriene → 6,10-Dimethylundeca-2,5,9-trien-4-one

HRID 903296

Reaction equation

HRID 903296 reaction equation
[CH3:1][C:2]([CH2:9][CH2:10][CH:11]=[C:12]([CH3:14])[CH3:13])=[CH:3][CH:4]([OH:8])[CH:5]=[CH:6][CH3:7]>O=[Mn]=O.C(Cl)Cl>[CH3:1][C:2]([CH2:9][CH2:10][CH:11]=[C:12]([CH3:13])[CH3:14])=[CH:3][C:4](=[O:8])[CH:5]=[CH:6][CH3:7]

Participants

4

Reactant 1

HCID 545494456,10-Dimethyl-4-hydroxy-2,5,9-undecatriene

Product 1

HCID 541583646,10-Dimethylundeca-2,5,9-trien-4-one

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

60 g. of the alcohol prepared according to paragraph (b) above, 700 g. of MnO2 and 1800 ml. of CH2Cl2 were stirred for 2 days at 20°-25°. After filtration and evaporation, the distillation of the residue gave 49 g. of crude ketone, b.p. 70°-75°/0.1 Torr, which was purified by vapour phase chromatography using a "20 M Carbowax" column and helium carrier at 140°. nD20 =1.5041; d420 =0.8958.

Workup

  1. filtrationAfter filtration and evaporation
  2. distillationthe distillation of the residue
  3. customgave 49 g
  4. customof crude ketone, b.p. 70°-75°/0.1 Torr, which was purified by vapour phase chromatography
  5. customat 140°

Sources & evidence

ORD record
ord-118d7d5fb7df47af8e06772df4a6d9f5
Source dataset
uspto-grants-1980_10
Patent number
US04226892

Linked notes

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