Sec butyloxycarbonyl methylene triphenylphosphorane → Sec butyl 4-(p-trifluoromethylphenoxy)cinnamate

HRID 463509Notes

Reaction equation

HRID 463509 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:17]=[CH:16][C:6]([O:7][C:8]2[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.[CH:20]([O:24][C:25]([CH:27]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:26])([CH2:22][CH3:23])[CH3:21]>ClCCl>[F:1][C:2]([F:19])([F:18])[C:3]1[CH:17]=[CH:16][C:6]([O:7][C:8]2[CH:15]=[CH:14][C:11]([CH:12]=[CH:27][C:25]([O:24][CH:20]([CH2:22][CH3:23])[CH3:21])=[O:26])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 13076692Sec butyloxycarbonyl methylene triphenylphosphoraneHCID 133008444-(4-(Trifluoromethyl)phenoxy)benzaldehyde

Product 1

HCID 86740131Sec butyl 4-(p-trifluoromethylphenoxy)cinnamateYield 97.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4(p-trifluoromethylphenoxy)benzaldehyde (30 g) and sec butyloxycarbonyl methylene triphenylphosphorane (50 g) dissolved in dichloromethane was allowed to stand for 1 hour at room temperature. After evaporation of the solvent the white solid was tritiated with petroleum ether to give a solution which on evaporation yielded sec butyl 4-(p-trifluoromethylphenoxy)cinnamate (40 g) b.p. 150°/0.007 mm.

Workup

  1. customAfter evaporation of the solvent the white solid
  2. customto give a solution which
  3. customon evaporation

Sources & evidence

ORD record
ord-f085e2f4528540f3b0b32dc4897af7c9
Source dataset
uspto-grants-1985_05
Patent number
US04520007

Reaction notes

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