Thionyl Chloride → HCID 15676328, compound

HRID 1111324Notes

Reaction equation

HRID 1111324 reaction equation
[F:1][C:2]([CH:4](O)[C:5]#[C:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[CH2:3].S(Cl)([Cl:14])=O>CCCCCC.CN(C)C=O>[F:1][C:2]([CH:4]([Cl:14])[C:5]#[C:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[CH2:3]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 15676316HCID 15676316, compound

Product 1

HCID 15676328HCID 15676328, compoundYield 90.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8058HexaneSolvent

Procedure

Ten grams (0.064 mole) of 2-fluoro-3-hydroxy-6,6-dimethylhept-1-ene-4-yne was dissolved in 100 ml of hexane, and 50 mg (6.8×10-4 mole) of N,N-dimethylformamide and 11.42 g (0.095 mole) of thionyl chloride were added to the resulting solution. The mixture was reacted overnight at room temperature with stirring with a hydrogen chloride gas trap mounted on the reactor. The reaction mixture was concentrated under reduced pressure. The resulting oily product was distilled under reduced pressure to obtain 10.1 g of 2-fluoro-3-chloro-6,6-dimethylhept-1-ene-4-yne.

Workup

  1. customThe mixture was reacted overnight at room temperature
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. distillationThe resulting oily product was distilled under reduced pressure

Sources & evidence

ORD record
ord-8f96283c52ba4e9e8cb5e86a7e60a4a9
Source dataset
uspto-grants-1990_12
Patent number
US04980345

Reaction notes

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