Pyridine → HCID 178445619, compound

HRID 1707532Notes

Reaction equation

HRID 1707532 reaction equation
[CH2:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11]O)[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].N1C=CC=CC=1.O=S(Cl)[Cl:21]>>[CH2:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][Cl:21])[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 178445651HCID 178445651, compound

Product 1

HCID 178445619HCID 178445619, compoundYield 90.9%

Procedure

37 g (0.22 mol) of trans-4-butylcyclohexylmethanol and 18 g (0.23 mol) of anhydrous pyridine were given dropwise addition of 32 g (0.27 mol) of SOCl2 in an ice water bath while stirring, and then stirred for 3 hours at 105°-110° C. with a mantle heater. The reactant was cooled to room temperature, poured into a beaker containing concentrated HC1 and ice, the oily layer was taken off, the water layer was extracted with chloroform, combined with the oily layer and washed with 10% HCl and water. The chloroform was extracted, and the remaining oily substance was distilled under reduced pressure (b. p. 80° C./3 mmHg) to obtain 38 g (0.20 mol) of trans-4-butylcyclohexylchloromethane.

Workup

  1. stirringstirred for 3 hours at 105°-110° C. with a mantle heater
  2. additionpoured into a beaker
  3. additioncontaining
  4. concentrationconcentrated HC1 and ice
  5. extractionthe water layer was extracted with chloroform
  6. washwashed with 10% HCl and water
  7. extractionThe chloroform was extracted
  8. distillationthe remaining oily substance was distilled under reduced pressure (b. p. 80° C./3 mmHg)

Sources & evidence

ORD record
ord-a4ea0d41ee234719bae1dd8bf6bd9819
Source dataset
uspto-grants-1994_10
Patent number
US05354502

Reaction notes

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