Chromic Acid → HCID 21553507, compound

HRID 268117Notes

Reaction equation

HRID 268117 reaction equation
[CH2:1]=[C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[CH:3]1[CH:10]([OH:14])[C:11]#[C:12][CH3:13].[Cr](O)(O)(=O)=O>O>[CH2:1]=[C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[CH:3]1[C:10](=[O:14])[C:11]#[C:12][CH3:13]

Participants

4

Reactant 2

HCID 24425Chromic AcidHCID 21553504HCID 21553504, compound

Product 1

HCID 21553507HCID 21553507, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

4.85 g of 2-methylene-6,6-dimethyl-1-[1-hydroxy-but-2-ynyl]-cyclohexane [which can be prepared according to the method described in example 5] (25 millimoles) in 30 ml of a mixture of ether-hexane 1:1 were added dropwise, while stirring, within 30 minutes to an ice-cooled solution of 24 g of chromic acid (0.25N) in 24 ml of water and 15 ml of a mixture of ether-hexane 1:1. The whole was allowed to stand for 24 hours at room temperature, while stirring vigorously, and then diluted with water. The reaction mixture was extracted with pentane, and the organic extracts, after the usual treatments of washing, drying and concentration, gave a residue which, by fractional distillation under reduced pressure, yielded 3.46 g (72 %) of the desired ketone; b.p. 66°-70°/0.03 Torr. An analytical sample was purified by means of vapour phase chromatography (1.25 m, 15 % CARBOWAX, 130°).

Workup

  1. additionwere added dropwise
  2. extractionThe reaction mixture was extracted with pentane
  3. washthe organic extracts, after the usual treatments of washing
  4. customdrying
  5. concentrationconcentration
  6. customgave a residue which
  7. distillationby fractional distillation under reduced pressure

Sources & evidence

ORD record
ord-d0f12c56953a4454bf3b0ee7b1c7536f
Source dataset
uspto-grants-1976_03
Patent number
US03946078

Reaction notes

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