Thionyl Chloride → HCID 178447872, compound

HRID 1589740Notes

Reaction equation

HRID 1589740 reaction equation
[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]2[CH:17]=[CH:16][C:13]([CH2:14]O)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].O=S(Cl)[Cl:20]>>[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]2[CH:17]=[CH:16][C:13]([CH2:14][Cl:20])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)[CH2:2][CH3:3]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 178447882HCID 178447882, compound

Product 1

HCID 178447872HCID 178447872, compoundYield 91.8%

Procedure

114 g (0.49 mol) of 4-(trans-4'-propylcyclohexyl) benzyl alcohol was dissolved in 107 cm3 (1.05 mol) of SOCl2 and the solution was refluxed over a warm water bath for 5 hours. The excess SOCl2 was distilled off under reduced pressure and the residue was washed with 10% hydrochloric acid and water. The chloroform was distilled off under reduced pressure and the residue was distilled under reduced pressure (147° C./3.0 mmHg) to yield 114 g (0.45 mol) of 4-(trans-4'-propylcyclohexyl)-benzyl chloride.

Workup

  1. temperaturethe solution was refluxed over a warm water bath for 5 hours
  2. distillationThe excess SOCl2 was distilled off under reduced pressure
  3. washthe residue was washed with 10% hydrochloric acid and water
  4. distillationThe chloroform was distilled off under reduced pressure
  5. distillationthe residue was distilled under reduced pressure (147° C./3.0 mmHg)

Sources & evidence

ORD record
ord-62bdf768ee7940cf9211c97fe331cada
Source dataset
uspto-grants-1993_04
Patent number
US05200110

Reaction notes

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