Toluene → HCID 54300281, compound

HRID 2073648Notes

Reaction equation

HRID 2073648 reaction equation
[C:1]([C:4]1[CH:16]=[CH:15][C:7]([CH:8]=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:5]=1)(O)=[O:2].S(Cl)([Cl:19])=O.C1(C)C=CC=CC=1>CN(C)C=O>[Cl:19][C:1]([C:4]1[CH:16]=[CH:15][C:7]([CH:8]=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:5]=1)=[O:2]

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 54303311HCID 54303311, compound

Product 1

HCID 54300281HCID 54300281, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

14.8 g (67 mmols) of ethyl 4-carboxycinnamate, 9.57 g (80 mmols) of thionyl chloride, 100 ml of toluene and 0.18 ml of N,N-dimethylformamide are boiled under reflux for 30 minutes. The reaction mixture is evaporated and the crude product is recrystallised from n-hexane. 12.6 g (79% of theory) of ethyl 4-chloroformylcinnamate are obtained in the form of white crystals; melting point 76.8° C.

Workup

  1. temperatureunder reflux for 30 minutes
  2. customThe reaction mixture is evaporated
  3. customthe crude product is recrystallised from n-hexane

Sources & evidence

ORD record
ord-ab7174e070c74254933145506e7b09e9
Source dataset
uspto-grants-1990_04
Patent number
US04918215

Reaction notes

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