Dichloromethane → 1547036-81-6

HRID 2171805Notes

Reaction equation

HRID 2171805 reaction equation
[CH3:1][C:2]1([CH3:11])[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9][OH:10])[CH2:4][CH2:3]1.C(Cl)Cl>CS(C)=O>[CH3:1][C:2]1([CH3:11])[CH2:3][CH2:4][CH:5]([CH2:8][CH:9]=[O:10])[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 149767172-(4,4-Dimethylcyclohexyl)ethan-1-ol

Product 1

HCID 235909341547036-81-6Yield 109.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
10 °C

Procedure

Under an argon atmosphere, to a mixture of 2-(4,4-dimethylcyclohexyl)ethanol (25.3 g) and DCM (200 mL) were added DMSO (50 mL) and TEA (100 mL), and a sulfur trioxide-pyridine complex (77.7 g) was added in small divided portions while maintaining the inner temperature to 10° C. or lower under ice-cooling. After stirring at room temperature for 2 hours, to the reaction mixture was added ice water, followed by concentration under reduced pressure and then extraction with chloroform. The organic layer was washed sequentially with 1 M hydrochloric acid and brine. To the organic layer was added MgSO4, followed by stirring. Then, the mixture was filtered and concentrated under reduced pressure to obtain (4,4-dimethylcyclohexyl)acetaldehyde (27.3 g).

Workup

  1. additiona sulfur trioxide-pyridine complex (77.7 g) was added
  2. temperaturelower under ice-cooling
  3. concentrationfollowed by concentration under reduced pressure
  4. extractionextraction with chloroform
  5. washThe organic layer was washed sequentially with 1 M hydrochloric acid and brine
  6. additionTo the organic layer was added MgSO4
  7. stirringby stirring
  8. filtrationThen, the mixture was filtered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a4d6aa0fd8db45f8b423965f28242c9a
Source dataset
uspto-grants-2015_06
Patent number
US09051339B2

Reaction notes

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