Thionyl Chloride → 3-(2,6-Dichlorophenyl)prop-2-enoyl chloride

HRID 463782Notes

Reaction equation

HRID 463782 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:7]=1[CH:8]=[CH:9][C:10](O)=[O:11]>C1(C)C=CC=CC=1>[Cl:5][C:6]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:7]=1[CH:8]=[CH:9][C:10]([Cl:3])=[O:11]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 95321(2e)-3-(2,6-Dichlorophenyl)acrylic acid

Product 1

HCID 403983-(2,6-Dichlorophenyl)prop-2-enoyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 20% thionyl chloride in toluene is added dropwise to a magnetically stirred, warmed mixture of 2,6-dichlorocinnamic acid (20.74 g) in toluene (119 ml) and the mixture brought to reflux for 6 hrs after it clears to a yellow haze. The reaction mixture is cooled overnight, filtered and concentrated in vacuo to afford a pale yellow solid, M.P. 64.5°-66° C.

Workup

  1. temperaturewarmed
  2. temperatureto reflux for 6 hrs after it
  3. temperatureThe reaction mixture is cooled overnight
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto afford a pale yellow solid, M.P. 64.5°-66° C.

Sources & evidence

ORD record
ord-2a9905dcf8d14dd6913298862a2d2c3e
Source dataset
uspto-grants-1985_10
Patent number
US04544670

Reaction notes

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