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

HRID 261840

Reaction equation

HRID 261840 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-50c25652e31947179f17951899bb060c
Source dataset
uspto-grants-1979_05
Patent number
US04152455

Linked notes

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