Thionyl Chloride → 1-Methylene-2,2,5,5-tetramethylcyclopentane

HRID 231726Notes

Reaction equation

HRID 231726 reaction equation
[CH3:1][C:2]1(O)[C:6]([CH3:8])([CH3:7])[CH2:5][CH2:4][C:3]1([CH3:10])[CH3:9].S(Cl)(Cl)=O>N1C=CC=CC=1>[CH2:1]=[C:2]1[C:6]([CH3:8])([CH3:7])[CH2:5][CH2:4][C:3]1([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 200340841,2,2,5,5-Pentamethylcyclopentanol

Product 1

HCID 140288511-Methylene-2,2,5,5-tetramethylcyclopentaneYield 40.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

30 g of 1,2,2,5,5-pentamethylcyclopentanol was dissolved in 150 ml of pyridine, and 20 ml of thionyl chloride was added dropwise thereto with ice cooling. The reaction mixture was stirred overnight and subjected to filtration. Ether and water were added to the filtrate, and the resulting layers were separated. The organic layer was washed twice with 200 ml of water, and then dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure, whereby 10.8 g of 1-methylene-2,2,5,5-tetramethylcyclopentane was obtained (b.p. 137°-140° C./760 mmHg).

Workup

  1. filtrationsubjected to filtration
  2. additionEther and water were added to the filtrate
  3. customthe resulting layers were separated
  4. washThe organic layer was washed twice with 200 ml of water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-73add0548bd54f7f8d11c9042f7d8fff
Source dataset
uspto-grants-1989_07
Patent number
US04847390

Reaction notes

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