3',4'-Dimethoxycinnamic acid → (2E)-3-(3,4-dimethoxyphenyl)prop-2-enoyl chloride

HRID 2175687Notes

Reaction equation

HRID 2175687 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]([OH:15])=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].S(Cl)([Cl:18])=O>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:11]=[CH:12]/[C:13]([Cl:18])=[O:15])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 168483',4'-Dimethoxycinnamic acidHCID 24386Thionyl Chloride

Product 1

HCID 11806394(2E)-3-(3,4-dimethoxyphenyl)prop-2-enoyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 3-(3,4-dimethoxyphenyl)acrylic acid (416 mg 2 mmol) in toluene (10 mL) was added thionyl chloride (1.45 mL, 20 mmol). The solution was heated at 50° C. for 1 hour and then the solvent was removed under reduced pressure to give (E)-3-(3,4-dimethoxyphenyl)acryloyl chloride, which was used directly in the next step without purification.

Workup

  1. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-de4ba91e67ba498987467ac2a849893c
Source dataset
uspto-grants-2015_06
Patent number
US09062076B2

Reaction notes

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