Thionyl Chloride → (E)-4,4-dimethyl-2-pentenoyl chloride

HRID 382541Notes

Reaction equation

HRID 382541 reaction equation
[CH3:1][C:2]([CH3:9])([CH3:8])/[CH:3]=[CH:4]/[C:5](O)=[O:6].S(Cl)([Cl:12])=O>C1C=CC=CC=1>[CH3:1][C:2]([CH3:9])([CH3:8])/[CH:3]=[CH:4]/[C:5]([Cl:12])=[O:6]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 5282660(2E)-4,4-Dimethyl-2-pentenoic acid

Product 1

HCID 22736682(E)-4,4-dimethyl-2-pentenoyl chloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of (E)-4,4-dimethyl-2-pentenoic acid (Gream, G. E.; Serelis, A. K. Aust. J. Chem. 1978, 31, 863) (200 mg, 1.6 mmol) in benzene (10 ml) was added thionyl chloride (0.5 ml) and the mixture was heated to reflux for 60 min. Volatiles were removed by evaporation to give crude (E)-4,4-dimethyl-2-pentenoyl chloride. Free base of the titled compound was prepared from N-(2-pyridyl)-o-phenylenediamine (150 mg, 0.81 mmol) and (E)-4,4-dimethyl-2-pentenoyl chloride obtained as above according to the preparation of (E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole (Example 1, method A). The free base was dissolved with a 10% methanol solution of hydrogen chloride (5 ml). Concentration and recrystallization from ethyl acetate yielded the titled compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 60 min
  3. customVolatiles were removed by evaporation

Sources & evidence

ORD record
ord-90e01ea347bb4e40afa4858d2551c43f
Source dataset
uspto-grants-2001_10
Patent number
US06310079B1

Reaction notes

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