Thionyl Chloride → 1-Chloro-6,6-dimethyl-2-hepten-4-yne

HRID 1493363Notes

Reaction equation

HRID 1493363 reaction equation
O[CH:2]([C:5]#[C:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH:3]=[CH2:4].S(Cl)([Cl:13])=O>CCCCCC.CN(C)C=O>[Cl:13][CH2:4][CH:3]=[CH:2][C:5]#[C:6][C:7]([CH3:10])([CH3:9])[CH3:8]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 109755616,6-dimethylhept-1-en-4-yn-3-ol

Product 1

HCID 248201731-Chloro-6,6-dimethyl-2-hepten-4-yneYield 88.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8058HexaneSolvent

Procedure

Ten grams (0.072 mole) of 3-hydroxy-6,6-dimethylhept-1-ene-4-yne was dissolved in 100 ml of hexane, and to the resulting solution were added 50 mg (6.8×10-4 mole) of N,N-dimethylformamide and 12.80 g (0.108 mole) of thionyl chloride. 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 to obtain 10 g of a crude 1-chloro-6,6-dimethylhept-2-ene-4-yne.

Workup

  1. customThe mixture was reacted overnight at room temperature
  2. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-49040d333bef4d15aebeafbf9830264d
Source dataset
uspto-grants-1991_06
Patent number
US05021446

Reaction notes

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