Toluene → 4-(2-Phenylethenyl)benzoyl chloride

HRID 2073642Notes

Reaction equation

HRID 2073642 reaction equation
[C:1]1([CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][C:4]([C:7](O)=[O:8])=[CH:3][CH:2]=1.S(Cl)([Cl:20])=O.C1(C)C=CC=CC=1>CN(C)C=O>[C:1]1([CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][C:4]([C:7]([Cl:20])=[O:8])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 5162089HCID 5162089, compound

Product 1

HCID 538172884-(2-Phenylethenyl)benzoyl chlorideYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

15.1 g (67.4 mmols) of stilbene-4-carboxylic acid, 10.0 g (84.25 mmols) of thionyl chloride, 150 ml of toluene and 0.18 ml of N,N-dimethylformamide are stirred at 70° C. for 3 hours. The reaction mixture is then evaporated and the crude product is recrystallised from n-hexane/cyclohexane. 13.7 g (84% of theory) of stilbene-4-carboxylic acid chloride are obtained in the form of white crystals; melting point 131.2° C.

Workup

  1. customThe reaction mixture is then evaporated
  2. customthe crude product is recrystallised from n-hexane/cyclohexane

Sources & evidence

ORD record
ord-304ea038ff9645ef97ab479614790942
Source dataset
uspto-grants-1990_04
Patent number
US04918215

Reaction notes

Loading…