Water → HCID 21333565, compound

HRID 1390647Notes

Reaction equation

HRID 1390647 reaction equation
[CH3:1][C:2]1([CH3:14])[CH:7]2[CH2:8][CH2:9][CH:4]([CH:5]([CH2:10][CH2:11]O)[CH2:6]2)[C:3]1=[O:13].S(Cl)([Cl:17])=O.O>N1C=CC=CC=1>[CH3:1][C:2]1([CH3:14])[CH:7]2[CH2:8][CH2:9][CH:4]([CH:5]([CH2:10][CH2:11][Cl:17])[CH2:6]2)[C:3]1=[O:13]

Participants

5

Reactant 3

HCID 962WaterHCID 24386Thionyl ChlorideHCID 21333572HCID 21333572, compound

Product 1

HCID 21333565HCID 21333565, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 50 g of 3,3-dimethyl-6-(2-hydroxyethyl)-bicyclo(2.2.2)-octan-2-one (produced according to Example II) in 200 ml of dry pyridine is added 30 g of thionyl chloride. The mixture is stirred at 50° C. for 2 hours and then poured into 50 g of water. The resulting aqueous solution is extracted with three 200 ml portions of ether. The combined ether layers are washed with two 100 ml portions of 5% aqueous HCl and dried over anhydrous sodium sulfate. The ether is stripped and the residue is vacuum distilled, yielding about 42 g of 3,3-dimethyl-6-(2-chloroethyl)-bicyclo(2.2.2)-octan-2-one, having the structure: ##STR28##

Workup

  1. extractionThe resulting aqueous solution is extracted with three 200 ml portions of ether
  2. washThe combined ether layers are washed with two 100 ml portions of 5% aqueous HCl
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationdistilled

Sources & evidence

ORD record
ord-1ef55f51157b4363ba6acc0a013d07cd
Source dataset
uspto-grants-1979_02
Patent number
US04139650

Reaction notes

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