Toluene → 2,3,4-Trimethoxy-6-methylbenzoyl cyanide

HRID 243791Notes

Reaction equation

HRID 243791 reaction equation
S(Cl)(Cl)=O.[CH3:5][O:6][C:7]1[C:15]([O:16][CH3:17])=[C:14]([O:18][CH3:19])[CH:13]=[C:12]([CH3:20])[C:8]=1[C:9]([OH:11])=O.C1(C)C=CC=CC=1.[Cu][C:29]#[N:30]>C(#N)C>[CH3:5][O:6][C:7]1[C:15]([O:16][CH3:17])=[C:14]([O:18][CH3:19])[CH:13]=[C:12]([CH3:20])[C:8]=1[C:9]([C:29]#[N:30])=[O:11]

Participants

6

Reactant 4

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 135314152,3,4-Trimethoxy-6-methylbenzoic acidHCID 178418546HCID 178418546, compound

Product 1

HCID 231336512,3,4-Trimethoxy-6-methylbenzoyl cyanideYield 45%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

10 ml of thionyl chloride was added to 6.0 g (26.6 mmol) of 2,3,4-trimethoxy-6-methylbenzoic acid, followed by stirring under reflux with heating for 4 hours, and the surplus thionyl chloride was distilled off under reduced pressure. 20 ml of toluene, 8 ml of acetonitrile and 3.1 g (34.5 mmol) of copper(I) cyanide were added, followed by stirring under reflux with heating for 16 hours. After cooling to room temperature, the reaction solution was subjected to filtration on the pad of celite, and the solvent was distilled off under reduced pressure. The crude product was purified by silica gel column chromatography to obtain 2.8 g (yield: 45%) of 2,3,4-trimethoxy-6-methylbenzoyl cyanide.

Workup

  1. temperatureunder reflux
  2. temperaturewith heating for 4 hours
  3. distillationthe surplus thionyl chloride was distilled off under reduced pressure
  4. stirringby stirring
  5. temperatureunder reflux
  6. temperaturewith heating for 16 hours
  7. filtrationthe reaction solution was subjected to filtration on the pad of celite
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-19301e01594c4bb1bcf8635ff1417485
Source dataset
uspto-grants-2014_02
Patent number
US08653277B2

Reaction notes

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