Thionyl Chloride → 3-(3-Methoxy-4-methylphenyl)acryloyl chloride

HRID 1366750Notes

Reaction equation

HRID 1366750 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][C:16]([OH:18])=O)[CH:10]=[CH:11][C:12]=1[CH3:13]>C1(C)C=CC=CC=1>[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][C:16]([Cl:3])=[O:18])[CH:10]=[CH:11][C:12]=1[CH3:13]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 534017143-Methoxy-4-methylcinnamic acid

Product 1

HCID 866129803-(3-Methoxy-4-methylphenyl)acryloyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Toluene (750 ml) and thionyl chloride (11 ml) were subsequently added to 3-(3-methoxy-4-methylphenyl)acrylic acid (20 g, 0.104 mol) at room temperature. The suspension was refluxed for 2 h while vigorously stirring to give a clear slightly yellow solution. The reaction mixture was concentrated in vacuo, then toluene added and the mixture re-concentrated in vacuo to give 3-(3-methoxy-4-methylphenyl)acryloyl chloride for use in the next step.

Workup

  1. temperatureThe suspension was refluxed for 2 h
  2. customto give a clear slightly yellow solution
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. additiontoluene added
  5. concentrationthe mixture re-concentrated in vacuo

Sources & evidence

ORD record
ord-62b9e671362f47d684ee2cfbaa83eba0
Source dataset
uspto-grants-2011_02
Patent number
US07893088B2

Reaction notes

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