Trifluoroacetic acid → 3-(4-Cyanophenyl)-propionic acid

HRID 485276Notes

Reaction equation

HRID 485276 reaction equation
C([O:5][C:6]([CH2:8][CH2:9][C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=1)=[O:7])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[OH:7][C:6]([CH2:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:14]#[N:15])=[CH:16][CH:17]=1)=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 202699291,1-Dimethylethyl 4-cyanobenzenepropanoate

Product 1

HCID 93617423-(4-Cyanophenyl)-propionic acidYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 2.31 g portion of 4-(2-t-butoxycarbonylethyl)-benzonitrile was admixed with 3 ml of trifluoroacetic acid and 30 ml of methylene chloride. The mixture was stirred at room temperature for 13 hours and concentrated. The resulting concentrate was subjected to azeotropic distillation with use of toluene, giving 1.75 g (yield 100%) of crude 4-(2-hydroxycarbonylethyl)benzonitrile. This compound was used for the subsequent reaction without purification.

Workup

  1. concentrationconcentrated
  2. concentrationThe resulting concentrate
  3. distillationwas subjected to azeotropic distillation with use of toluene

Sources & evidence

ORD record
ord-ff5c8425ae3c402b9541367a8882ac34
Source dataset
uspto-grants-1985_08
Patent number
US04536391

Reaction notes

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