Thionyl Chloride → 5-Benzyl-1-cyclooctanol

HRID 498101Notes

Reaction equation

HRID 498101 reaction equation
[CH2:1]([C:8]1(O)[CH2:15][CH2:14][CH2:13][CH:12](C(C)(C)C)[CH2:11][CH2:10][CH:9]1O[SiH](C)C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=[O:26]>N1C=CC=CC=1>[CH2:1]([CH:8]1[CH2:15][CH2:14][CH2:13][CH:12]([OH:26])[CH2:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 1317251671-Benzyl-5-(tert-butyl)dimethylsilyloxy-1-cyclooctanol

Product 1

HCID 223197855-Benzyl-1-cyclooctanol

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

1.7 g of the above product (b) was dissolved in 40 ml of pyridine. To the solution was added 0.43 ml of thionyl chloride while cooling with an ice bath. After stirring at 0° C. for twenty minutes, the reaction solution was poured into ice water, and extracted with ether. The organic layer was washed with a saturated saline solution, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, to afford 1.6 g of the titled compound as pale yellow liquid.

Workup

  1. temperaturewhile cooling with an ice bath
  2. extractionextracted with ether
  3. washThe organic layer was washed with a saturated saline solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-5c5780bd0aef4c7aa8ec10ff505b30ca
Source dataset
uspto-grants-2005_09
Patent number
US06949585B2

Reaction notes

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