Oxalyl chloride → Cinnamoyl Chloride

HRID 1378465Notes

Reaction equation

HRID 1378465 reaction equation
[C:1]([OH:11])(=O)/[CH:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(Cl)(=O)C([Cl:15])=O>C1(C)C=CC=CC=1>[C:1]([Cl:15])(=[O:11])/[CH:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 444539Cinnamic Acid

Product 1

HCID 5354261Cinnamoyl ChlorideYield 135.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

trans-Cinnamic acid (5 g, 33.7 mmol, Aldrich) was dissolved in toluene (100 mL), and the solution was cooled to 0° C. and flushed with N2. Anhydrous DMF (0.1 mL) was added, followed by oxalyl chloride (8.56 g, 5.88 mL, 67.4 mmol) dropwise over 8 minutes. The mixture was stirred at 0° C. for 1 hour and at room temperature for 1.5 hours. The solvent was removed under vacuum to give the title compound (7.63 g).

Workup

  1. customflushed with N2
  2. additionAnhydrous DMF (0.1 mL) was added
  3. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-e10c6885b10e4c409e4186dd97939b6d
Source dataset
uspto-grants-1997_09
Patent number
US05668164

Reaction notes

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