Thionyl Chloride → trans-1-Chloro-3-(3-ethyl-1-methylcyclobutyl)-prop-1-en-3-one

HRID 27300

Reaction equation

HRID 27300 reaction equation
O[CH:2]=[CH:3][C:4]([C:6]1([CH3:12])[CH2:9][CH:8]([CH2:10][CH3:11])[CH2:7]1)=[O:5].S(Cl)([Cl:15])=O>C1C=CC=CC=1>[Cl:15]/[CH:2]=[CH:3]/[C:4]([C:6]1([CH3:12])[CH2:9][CH:8]([CH2:10][CH3:11])[CH2:7]1)=[O:5]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 705764901-Hydroxy-3-(3-ethyl-1-methylcyclobutyl)-prop-1-en-3-one

Product 1

HCID 23344457trans-1-Chloro-3-(3-ethyl-1-methylcyclobutyl)-prop-1-en-3-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of 5.8 g of 1-hydroxy-3-(3-ethyl-1-methylcyclobutyl)-prop-1-en-3-one (prepared in Example 4A) in 100 ml of benzene was stirred under an argon atmosphere and 7 ml of thionyl chloride in 10 ml of benzene was added dropwise. The resulting solution was stirred for about 15 hr. Excess solvent was removed by distillation at atmospheric pressure and the residue was then distilled in vacuo to yield 4.2 g of the title compound having the following physical characteristics:

Workup

  1. customExcess solvent was removed by distillation at atmospheric pressure
  2. distillationthe residue was then distilled in vacuo

Sources & evidence

ORD record
ord-dfce49b24eef4f29acfdd572bdff2687
Source dataset
uspto-grants-1980_09
Patent number
US04220795

Linked notes

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