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

HRID 278518Notes

Reaction equation

HRID 278518 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-045d5c0f2ca94392b7ae4129fc78ef0e
Source dataset
uspto-grants-2002_03
Patent number
US06359156B1

Reaction notes

Loading…