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

HRID 261841

Reaction equation

HRID 261841 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., 38, 881 (1974), 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-2168c1c5860e41bcbe412bf4e1bd93fc
Source dataset
uspto-grants-1979_05
Patent number
US04152455

Linked notes

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