4-Methylbenzoyl Chloride → Oxo-P-tolyl-acetonitrile

HRID 379008

Reaction equation

HRID 379008 reaction equation
[Sn](Cl)(Cl)(Cl)Cl.[C:6]1([CH3:15])[CH:11]=[CH:10][C:9]([C:12](Cl)=[O:13])=[CH:8][CH:7]=1.[Si]([C:20]#[N:21])(C)(C)C>C(Cl)Cl>[C:6]1([CH3:15])[CH:11]=[CH:10][C:9]([C:12]([C:20]#[N:21])=[O:13])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 134054-Methylbenzoyl ChlorideHCID 24287Tin tetrachlorideHCID 82115Trimethylsilyl cyanide

Product 1

HCID 641326Oxo-P-tolyl-acetonitrileYield 93.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneCatalyst

Procedure

A 1 M solution of tin chloride in CH2Cl2 (1.3 mL, 1.3 mmol) was added dropwise to an ice water cooled solution of p-toluoyl chloride (10.00 g, 65 mmol) and TMSCN (9.00 mL, 68 mmol). The reaction was monitored to completion over 4 hours by disappearance of the IR acid chloride carbonyl stretch, then quenched by addition of ice water (20 mL) and extracted with CH2Cl2. The organic solution was dried (MgSO4) and concentrated to afford 8.80 g of p-toluoyl cyanide as an orange solid.

Workup

  1. customquenched by addition of ice water (20 mL)
  2. extractionextracted with CH2Cl2
  3. dry with materialThe organic solution was dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6a7d3c95abe34b609b25547ca31efbb4
Source dataset
uspto-grants-2001_10
Patent number
US06297271B1

Linked notes

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