Pyridine → alpha-Trifluoromethyl-3-phenoxybenzyl 3-(2,2-dimethylvinyl)-2,2-dimethylcyclopropanecarboxylate

HRID 972008

Reaction equation

HRID 972008 reaction equation
[CH3:1][C:2]1([CH3:12])[CH:4]([CH:5]=[C:6]([CH3:8])[CH3:7])[CH:3]1[C:9](Cl)=[O:10].[F:13][C:14]([F:31])([F:30])[CH:15]([OH:29])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:17]=1.N1C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:7][C:6]([CH3:8])=[CH:5][CH:4]1[CH:3]([C:9]([O:29][CH:15]([C:14]([F:13])([F:30])[F:31])[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:17]=2)=[O:10])[C:2]1([CH3:12])[CH3:1]

Participants

5

Reactant 3

HCID 1049PyridineHCID 26620(1R-trans)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarbonyl chlorideHCID 142705712,2,2-Trifluoro-1-(3-phenoxyphenyl)ethan-1-ol

Product 1

HCID 12855315alpha-Trifluoromethyl-3-phenoxybenzyl 3-(2,2-dimethylvinyl)-2,2-dimethylcyclopropanecarboxylateYield 93.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

This compound was prepared in the manner of Example II using 3.3 g of 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarbonyl chloride, whose preparation is described in J. Sci. Food and Agriculture, 18, 325 (1967), 4.3 g of α-trifluoromethyl-3-phenoxybenzyl alcohol, and 1.5 g of pyridine in 50 ml of toluene. Volatiles were distilled from the crude reaction product at 90°/0.08 mm for 1/2 hour, then at 100°/0.08 mm for 3/4 hour through a short path Kugelrohr distillation system to give as a residue 6.3 g of α-trifluoromethyl-3-phenoxybenzyl 3-(2,2-dimethylvinyl)-2,2-dimethylcyclopropanecarboxylate. The ir spectrum was consistent with the assigned structure.

Workup

  1. customThis compound was prepared in the manner of Example II
  2. distillationVolatiles were distilled from the crude
  3. customreaction product at 90°/0.08 mm for 1/2 hour
  4. distillationat 100°/0.08 mm for 3/4 hour through a short path Kugelrohr distillation system

Sources & evidence

ORD record
ord-a7ee1ca9f5ec4af6a9783841f21d0c35
Source dataset
uspto-grants-1979_07
Patent number
US04162366

Linked notes

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