4-Methylpyridine → 2,2-Dimethyl-3-(2',2'-dichlorovinyl)-cyclopropanecarboxylic acid 2benzyl-(alpha-vinyl)-benzyl ester

HRID 67124

Reaction equation

[CH3:1][C:2]1([CH3:12])[CH:4]([CH:5]=[C:6]([Cl:8])[Cl:7])[CH:3]1[C:9](Cl)=[O:10].N1C=CC(C)=CC=1.[CH2:20]([C:27]1[CH:36]=[CH:35][CH:34]=[CH:33][C:28]=1[CH:29]([OH:32])[CH:30]=[CH2:31])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CCOCC>[CH2:20]([C:27]1[CH:36]=[CH:35][CH:34]=[CH:33][C:28]=1[CH:29]([O:32][C:9]([CH:3]1[CH:4]([CH:5]=[C:6]([Cl:7])[Cl:8])[C:2]1([CH3:12])[CH3:1])=[O:10])[CH:30]=[CH2:31])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

Conditions

Temperature: 25 °C

Procedure

91 g (0.04 mole) of 2,2-dimethyl-3-(2',2'-dichlorovinyl)-cyclopropanecarboxylic acid chloride are added dropwise, whilst stirring, to 4.6 g (0.05 mole) of γ-picoline, 100 ml of absolute ether and 8.5 g (0.38 mole) of 2-benzyl-(α-vinyl)-benzyl alcohol at 0°-5° C. After having been stirred for 12 hours at 25° C., the reaction mixture is filtered and the filtrate is successively washed with 2 N sodium bicarbonate solution, 2 N hydrochloric acid and water. After drying over sodium sulfate, the filtrate is concentrated under reduced pressure and the resulting oil is purified by column chromatography over silica gel, using toluene as the eluant.

Workup

filtrationthe reaction mixture is filtered
washthe filtrate is successively washed with 2 N sodium bicarbonate solution, 2 N hydrochloric acid and water
dry with materialAfter drying over sodium sulfate
concentrationthe filtrate is concentrated under reduced pressure
customthe resulting oil is purified by column chromatography over silica gel

Sources & evidence

ORD record: ord-bc78c4a0c5b148f591dbeb66b6a477aa
Source dataset: uspto-grants-1982_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04344961

Linked notes

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