Thionyl Chloride → (1S,3S)-2,2-Dimethyl-3-(2-methyl-1-propen-1-yl)cyclopropanecarbonyl chloride

HRID 1729829Notes

Reaction equation

HRID 1729829 reaction equation
[CH3:1][C:2]1([CH3:12])[C@@H:4]([CH:5]=[C:6]([CH3:8])[CH3:7])[C@@H:3]1[C:9](O)=[O:10].S(Cl)([Cl:15])=O>CCCCC>[CH3:1][C:2]1([CH3:12])[C@@H:4]([CH:5]=[C:6]([CH3:8])[CH3:7])[C@@H:3]1[C:9]([Cl:15])=[O:10]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 33607(1S-trans)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid

Product 1

HCID 54401499(1S,3S)-2,2-Dimethyl-3-(2-methyl-1-propen-1-yl)cyclopropanecarbonyl chlorideYield 97.1%

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

In a 300 ml flask, there were charged n-pentane (100 ml) and (-)-trans-2,2-dimethyl-3-isobutenylcyclopropane-1-carboxylic acid (50.0 g), and thionyl chloride (46.0 g) was added thereto from a dropping funnel in 20 minutes with stirring under reflux. After completion of the addition, stirring was continued for a further 3 hours, and then the solvent and excess of the thionyl chloride were removed by distillation. The residue was distilled to give (-)-trans-2,2-dimethyl-3-isobutenylcyclopropane-1-carboxylic acid chloride (53.9 g) having a boiling point of 50° C/0.5 mmHg - 56° C/0.6 mmHg. Other cyclopropanecarboxylic acid halides were prepared in the same manner as above.

Workup

  1. additionwas added
  2. temperatureunder reflux
  3. additionAfter completion of the addition
  4. stirringstirring
  5. waitwas continued for a further 3 hours
  6. customthe solvent and excess of the thionyl chloride were removed by distillation
  7. distillationThe residue was distilled

Sources & evidence

ORD record
ord-b82f5bd5c86041eda97172d950b84a95
Source dataset
uspto-grants-1976_11
Patent number
US03989750

Reaction notes

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