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

HRID 50901Notes

Reaction equation

HRID 50901 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. MW: 313.83; mp: 171.0-172.3° C.; 1H-NMR (CDCl3) δ: 8.86-8.82 (1H, m), 8.27 (1H, d, J=16.3 Hz), 8.21-8.13 (2H, m), 7.72-7.65 (1H, m), 7.62-7.43 (4H, m), 6.31 (1H, d, J=16.3 Hz), 1.17 (9H, s).

Workup

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

Sources & evidence

ORD record
ord-32e6d2db25394213906bf1e37f7a6110
Source dataset
uspto-grants-2004_03
Patent number
US06713482B2

Reaction notes

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