Oxalyl chloride → Cinnamic Acid

HRID 1283487Notes

Reaction equation

HRID 1283487 reaction equation
[C:1]([OH:11])(=[O:10])/[CH:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(Cl)(=O)C(Cl)=O>C1C=CC=CC=1>[C:1]([OH:11])(=[O:10])/[CH:2]=[CH:3]/[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1.[C:1]([O-:11])(=[O:10])/[CH:2]=[CH:3]/[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 444539Cinnamic Acid

Product 2

HCID 444539Cinnamic AcidHCID 59577284151-45-5

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 3.05 g. of trans-cinnamic acid in dry benzene is added 5 ml of oxalyl chloride. The reaction mixture is stirred at room temperature, under nitrogen, for 2 hours. Solvent is removed in vacuo and replaced by fresh dry benzene and 3.9 ml. of cyclopropanemethyl alcohol is added. The reaction mixture is stirred overnight at room temperature, under nitrogen. The reaction is worked up by washing with water and brine, drying over calcium sulfate and evaporating under reduced pressure and fractionally distilling to yield the cyclopropanemethyl ester of trans-cinnamic acid, (cyclopropanemethyl trans-cinnamate) b.p. 100° (bath) at .1 mm.

Workup

  1. customSolvent is removed in vacuo
  2. additionof cyclopropanemethyl alcohol is added
  3. stirringThe reaction mixture is stirred overnight at room temperature, under nitrogen
  4. washby washing with water and brine
  5. dry with materialdrying over calcium sulfate
  6. customevaporating under reduced pressure
  7. distillationfractionally distilling

Sources & evidence

ORD record
ord-d90453cc7d934271af1ac88dc114f049
Source dataset
uspto-grants-1976_08
Patent number
US03975429

Reaction notes

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