HCID 54279535, compound → HCID 54564502, compound

HRID 981017Notes

Reaction equation

HRID 981017 reaction equation
[CH2:1]([O:5][CH:6]1[CH:17]([OH:18])[CH2:16][CH2:15][CH:14]=[CH:13][CH2:12][CH2:11][CH:10]=[CH:9][CH2:8][CH2:7]1)[CH:2]([CH3:4])[CH3:3].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>ClCCl>[CH2:1]([O:5][CH:6]1[C:17](=[O:18])[CH2:16][CH2:15][CH:14]=[CH:13][CH2:12][CH2:11][CH:10]=[CH:9][CH2:8][CH2:7]1)[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 54279535HCID 54279535, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 54564502HCID 54564502, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.71 g of 12-isobutoxy-4,8-cyclododecadien-1-ol were dissolved in 50 ml of dichloromethane and 8 g of diatomaceous earth were added to this solution, in suspension. After stirring, 8.05 g of PCC were added in small portions, the reaction mixture having been kept under stirring, at room temperature, for 2 h. Afterwards, the chromium salts were precipitated with ethyl ether and the reaction mixture was filtered on SiO2 and concentrated. Distillation in a bulb-to-bulb apparatus gave 3.43 g of 12-isobutoxy-4,8-cyclododecadien-1-one.

Workup

  1. addition8 g of diatomaceous earth were added to this solution, in suspension
  2. stirringunder stirring, at room temperature, for 2 h
  3. customAfterwards, the chromium salts were precipitated with ethyl ether
  4. filtrationthe reaction mixture was filtered on SiO2
  5. concentrationconcentrated
  6. distillationDistillation in a bulb-to-bulb apparatus

Sources & evidence

ORD record
ord-1ce23c348ac449e8b2a4a7c19824706d
Source dataset
uspto-grants-1991_02
Patent number
US04990495

Reaction notes

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