Phosphorus oxychloride → Cyclohexylmethane sulfonyl chloride

HRID 264007Notes

Reaction equation

HRID 264007 reaction equation
[Na+].[CH:2]1([CH2:8][S:9]([O-:12])(=O)=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.O=P(Cl)(Cl)[Cl:15]>>[CH:2]1([CH2:8][S:9]([Cl:15])(=[O:12])=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 23693649HCID 23693649, compound

Product 1

HCID 3871475Cyclohexylmethane sulfonyl chloride

Conditions

Temperature
100 °C

Procedure

To the compound of Example 12 (4.0 g, 20 mmole) was added POCl3 (15 mL) and the mixture heated at 100° C. for 48 hours. Upon cooling to room temperature the mixture was poured onto crushed ice and then the aqueous phase was extracted with ethyl acetate (2×100 mL). The combined organic extracts were then washed with saturated aqueous sodium bicarbonate (2×50 mL), brine and then dried over MgSO4, filtered and the solvent was evaporated under vacuum to provide 3.46 g of the title compound as a light yellow oil. Thin layer chromatography analysis of the title compound showed a single spot with Rf =0.53 (silica, 4:1 hexanes/ethyl acetate).

Workup

  1. temperatureUpon cooling to room temperature the mixture
  2. additionwas poured
  3. customonto crushed ice
  4. extractionthe aqueous phase was extracted with ethyl acetate (2×100 mL)
  5. washThe combined organic extracts were then washed with saturated aqueous sodium bicarbonate (2×50 mL), brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customthe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-42fea478051c43138ac47531be6b43af
Source dataset
uspto-grants-1997_07
Patent number
US05646165

Reaction notes

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