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

HRID 2052167Notes

Reaction equation

HRID 2052167 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>CCCCCC>[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 97.3%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

In a 300 ml flask, there were charged (-)-trans-2,2-dimethyl-3-isobutenylcyclopropane-1-carboxylic acid (50.0 g) and n-hexane (50 g), and thionyl chloride (41.0 g) was added thereto from a dropping funnel over a period of 30 minutes with stirring under reflux. After completion of the addition, stirring was continued for an additional 2.5 hours, and then the solvent and excess of the thionyl chloride were removed by distillation. The residue was distilled to obtain (-)-trans-2,2-dimethyl-3-isobutenylcyclopropane-1-carboxylic acid chloride (54.0 g) having a boiling point of 50° C./0.5 mmHg to 56° C./0.6 mmHg.

Workup

  1. additionwas added
  2. temperatureunder reflux
  3. additionAfter completion of the addition
  4. stirringstirring
  5. waitwas continued for an additional 2.5 hours
  6. customthe solvent and excess of the thionyl chloride were removed by distillation
  7. distillationThe residue was distilled

Sources & evidence

ORD record
ord-bd24ab8afc6f40148c3d366832ee1520
Source dataset
uspto-grants-1980_01
Patent number
US04182906

Reaction notes

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