Oxalyl chloride → HCID 22609552, compound

HRID 2306782Notes

Reaction equation

HRID 2306782 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 185 mg (0.70 mmol) of 5-(3,4,5-trimethoxyphenyl)penta-(2E,4E)-dienoic acid in anhydrous dimethylformamide-methylene chloride (0.2 ml-2 ml) was cooled in an ice bath. To the solution was added 0.10 ml (1.1 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-dcd09598b0be4bf1a4fe4b0293e19d80
Source dataset
uspto-grants-2004_12
Patent number
US06828316B2

Reaction notes

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