Thionyl Chloride → HCID 13662670, compound

HRID 1112186Notes

Reaction equation

HRID 1112186 reaction equation
S(Cl)([Cl:3])=O.[C:5]12(O)[CH2:14][CH:10]([CH2:11][CH2:12][CH2:13]1)[CH:9]1[CH2:15][CH:6]2[CH2:7][CH2:8]1>C1C=CC=CC=1>[Cl:3][C:5]12[CH2:14][CH:10]([CH2:11][CH2:12][CH2:13]1)[CH:9]1[CH2:15][CH:6]2[CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 13070378HCID 13070378, compound

Product 1

HCID 13662670HCID 13662670, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Five milliliters of thionyl chloride are added to a solution of 5.0 g (30 millimoles) tricyclo [4.3.1.12,5 ] undecane-1-ol in 30 ml dry anhydrous benzene and the entirety is refluxed for 1.5 hours. The reaction mixture is concentrated under reduced pressure and there is further added 20 ml of dry benzene. Reduced pressure concentration is repeated to distill out the excess thionyl chloride completely. The residue is distilled under reduced pressure to collect a fraction boiling at 95° C./3mmHg, to obtain 5.0 g (yield 89%) of 1-chlorotricyclo [4.3.1.12,5 ] undecane.

Workup

  1. temperaturethe entirety is refluxed for 1.5 hours
  2. concentrationThe reaction mixture is concentrated under reduced pressure and there
  3. concentrationReduced pressure concentration
  4. distillationto distill out the excess thionyl chloride completely
  5. distillationThe residue is distilled under reduced pressure
  6. customto collect a fraction boiling at 95° C./3mmHg

Sources & evidence

ORD record
ord-bdfee4c40ce64dc496626979d73dfce5
Source dataset
uspto-grants-1978_10
Patent number
US04120906

Reaction notes

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