Thionyl Chloride → HCID 13662666, compound

HRID 903838Notes

Reaction equation

HRID 903838 reaction equation
S(Cl)([Cl:3])=O.[C:5]([C:8]12[CH2:17][CH:13]([CH2:14][CH2:15][CH2:16]1)[CH:12]1[CH2:18][CH:9]2[CH2:10][CH2:11]1)(O)=[O:6]>C1C=CC=CC=1>[Cl:3][C:5]([C:8]12[CH2:17][CH:13]([CH2:14][CH2:15][CH2:16]1)[CH:12]1[CH2:18][CH:9]2[CH2:10][CH2:11]1)=[O:6]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 54204432HCID 54204432, compound

Product 1

HCID 13662666HCID 13662666, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

68 ml of thionyl chloride was added dropwise to 46.0 g (0.24 mole) of 1-carboxytricyclo[4.3.1.12,5 ]undecane dissolved in 200 ml of benzene at room temperature. The resulting mixture was refluxed for 1.5 hours, and excess thionyl chloride and benzene were distilled off under reduced pressure. The residue obtained was fractionally distilled under reduced pressure to afford 47.0 g (yield: 92%) of 1-chlorocarbonyltricyclo[4.3.1.12,5 ]undecane having a boiling point of 101° C. (1 mmHg).

Workup

  1. temperatureThe resulting mixture was refluxed for 1.5 hours
  2. distillationexcess thionyl chloride and benzene were distilled off under reduced pressure
  3. customThe residue obtained
  4. distillationwas fractionally distilled under reduced pressure

Sources & evidence

ORD record
ord-dd1f23cda3e446d2ab641da8e4dc10e7
Source dataset
uspto-grants-1980_10
Patent number
US04229375

Reaction notes

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