Oxalyl chloride → HCID 22609552, compound

HRID 1368924Notes

Reaction equation

HRID 1368924 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:13]=[CH:14]/[CH:15]=[CH:16]/[C:17]([OH:19])=O)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].C(Cl)(=O)C([Cl:23])=O>CN(C)C=O.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:13]=[CH:14]/[CH:15]=[CH:16]/[C:17]([Cl:23])=[O:19])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 15257506HCID 15257506, compound

Product 1

HCID 22609552HCID 22609552, compound

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

A solution of 174 mg (0.66 mmol) of 5-(3,4,5-trimethoxyphenyl)penta-(2E,4E)-dienoic acid in anhydrous dimethylformamide-methylene chloride (0.1 ml-5 ml) was cooled in an ice bath, and to the solution was added 0.080 ml (0.92 mmol) of oxalyl chloride with stirring. The ice bath was removed, and the mixture was stirred for 30 minutes at room temperature. The reaction mixture was concentrated under reduced pressure to obtain crude crystals of 5-(3,4,5-trimethoxyphenyl)penta-(2E, 4E)-dienoyl chloride.

Workup

  1. customThe ice bath was removed
  2. stirringthe mixture was stirred for 30 minutes at room temperature
  3. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b672e62a73384d0c8a65c792103c6490
Source dataset
uspto-grants-2003_06
Patent number
US06576642B2

Reaction notes

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