Thionyl Chloride → HCID 13662666, compound

HRID 1413120Notes

Reaction equation

HRID 1413120 reaction equation
[C:1]12([C:12]([OH:14])=O)[CH2:10][CH:6]([CH2:7][CH2:8][CH2:9]1)[CH:5]1[CH2:11][CH:2]2[CH2:3][CH2:4]1.S(Cl)([Cl:17])=O>C1C=CC=CC=1>[Cl:17][C:12]([C:1]12[CH2:10][CH:6]([CH2:7][CH2:8][CH2:9]1)[CH:5]1[CH2:11][CH:2]2[CH2:3][CH2:4]1)=[O:14]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 54204432HCID 54204432, compound

Product 1

HCID 13662666HCID 13662666, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Into a solution of 5.5 g (0.028 mole) of tricyclo[4,3,1,12,5 ]undecane-1-carboxylic acid (IV) in 20 ml of dry benzene was added dropwise with stirring 12 ml of thionyl chloride at room temperature. The mixture was heated under reflux for one hour. Excess thionyl chloride and benzene were distilled off and the residue was fractionally distilled. A fraction boiling at 105° to 108° C. (2 mm Hg) was collected to give 5.2 g (87% yield) of 1-chlorocarbonyltricyclo[4,3,1,12,5 ]undecane. IR (neat):

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for one hour
  3. distillationExcess thionyl chloride and benzene were distilled off
  4. distillationthe residue was fractionally distilled
  5. customA fraction boiling at 105° to 108° C. (2 mm Hg) was collected

Sources & evidence

ORD record
ord-8ecc2559b2db4f3ba18ea7656b4d19cc
Source dataset
uspto-grants-1981_02
Patent number
US04248891

Reaction notes

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