Pyridine → alpha-Trifluoromethyl-3-phenoxybenzyl 2-(4-chlorophenyl)-3-methylbutanoate

HRID 972009Notes

Reaction equation

HRID 972009 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:12]([CH3:14])[CH3:13])[C:9](Cl)=[O:10])=[CH:4][CH:3]=1.[F:15][C:16]([F:33])([F:32])[CH:17]([OH:31])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:19]=1.N1C=CC=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:12]([CH3:14])[CH3:13])[C:9]([O:31][CH:17]([C:16]([F:15])([F:32])[F:33])[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:19]=2)=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 41780012-(4-Chlorophenyl)-3-methylbutanoyl chlorideHCID 142705712,2,2-Trifluoro-1-(3-phenoxyphenyl)ethan-1-ol

Product 1

HCID 53818390alpha-Trifluoromethyl-3-phenoxybenzyl 2-(4-chlorophenyl)-3-methylbutanoateYield 98.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

This compound was prepared in the manner of Example II, using 5.3 g of 2-(4-chlorophenyl)-3-methylbutanoyl chloride, whose preparation is described in Agr. Biol. Chem., 31, 1148 (1967), together with J. Kagaku To Seibutsu, 14, 427 (1976), 4.6 g of α-trifluoromethyl-3-phenoxybenzyl alcohol, and 1.5 g of pyridine in 50 ml of toluene. Volatiles were removed from the crude reaction product at 100° C./0.02 mm through a short path Kugelrohr distillation system to give as a residue 7.8 g of α-trifluoromethyl-3-phenoxybenzyl 2-(4-chlorophenyl)-3-methylbutanoate. The ir spectrum was consistent with the assigned structure.

Workup

  1. customThis compound was prepared in the manner of Example II
  2. customVolatiles were removed from the crude
  3. customreaction product at 100° C./0.02 mm
  4. distillationthrough a short path Kugelrohr distillation system

Sources & evidence

ORD record
ord-352c8a90814d44b7bf510ec885d5ce64
Source dataset
uspto-grants-1979_07
Patent number
US04162366

Reaction notes

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