Thionyl Chloride → HCID 15369663, compound

HRID 1522828

Reaction equation

HRID 1522828 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[C:12]([O:14][CH3:15])[CH:13]=1)/[CH:6]=[CH:7]/[C:8](O)=[O:9].S(Cl)([Cl:18])=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[C:12]([O:14][CH3:15])[CH:13]=1)/[CH:6]=[CH:7]/[C:8]([Cl:18])=[O:9]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 5324677(2E)-3-(3,5-Dimethoxyphenyl)-2-propenoic acid

Product 1

HCID 15369663HCID 15369663, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of trans-3,5-dimethoxycinnamic acid (15.30 g, 73.48 mmol) and thionyl chloride (13.11 g, 0.11 mol) were placed in a 250 mL single-necked round-bottomed flask fitted with a magnetic stirring bar and reflux condenser. Dry methylene chloride (80.0 mL) was added to the above mixture. The resulting solution was heated to reflux for 3 hours. Then, the solvent was removed under reduced pressure. The residue was dried under vacuum overnight to give a pale-yellow solid, trans-3,5-dimethoxycinnamic acid chloride.

Workup

  1. customwere placed in a 250 mL single-necked round-bottomed flask
  2. customfitted with a magnetic stirring bar
  3. temperaturereflux condenser
  4. temperatureThe resulting solution was heated
  5. temperatureto reflux for 3 hours
  6. customThen, the solvent was removed under reduced pressure
  7. customThe residue was dried under vacuum overnight

Sources & evidence

ORD record
ord-ef98c0adecc94cee9e1a16a877a85fe2
Source dataset
uspto-grants-2015_07
Patent number
US09078888B2

Linked notes

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