Water → 2-Methylbenzoyl cyanide

HRID 1721284Notes

Reaction equation

HRID 1721284 reaction equation
[C:1]1([CH3:10])[C:2]([C:7](Cl)=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.O.[C-:12]#[N:13].[Na+]>ClCCl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:10][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([C:12]#[N:13])=[O:8]

Participants

6

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 702762-Methylbenzoyl chloride

Product 1

HCID 98339902-Methylbenzoyl cyanide

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of o-toluoyl chloride (38.86 g) in dichloromethane (250 ml) at room temperature was added water (20.0 ml) followed immediately by tetrabutylammonium bromide (0.15 g) and sodium cyanide (13.0 g). The reaction mixture was stirred vigorously for 11/2 hours, then filtered. The filtrate was washed with water (2×100 ml) then dried (MgSO4) and evaporated under reduced pressure to give a golden oil. Distillation under vacuum gave 2-methylbenzoyl cyanide, as a colourless oil, bp 47°-50°/0.05 mm. To 85% w/w sulphuric acid (140 ml) at room temperature was added sodium bromide (20 g) followed immediately by the dropwise addition of 2-methylbenzoyl cyanide (34.8 g). The reaction mixture was then heated gently until the exothermic reaction started and then maintained at 70° C. for 10 minutes by cooling. Methanol (400 ml) was added and the mixture heated under reflux for 1 hour, cooled and diluted with ice/water (500 ml). Extraction with diethyl ether gave a golden oil which was distilled under vacuum to give methyl oxo(o-tolyl)acetate, as B colourless oil, bp 75°-85°/0.4 mm.

Workup

  1. filtrationfiltered
  2. washThe filtrate was washed with water (2×100 ml)
  3. dry with materialthen dried (MgSO4)
  4. customevaporated under reduced pressure
  5. customto give a golden oil
  6. distillationDistillation under vacuum

Sources & evidence

ORD record
ord-43b7efd500324e4eaedd85229938f782
Source dataset
uspto-grants-1996_04
Patent number
US05510344

Reaction notes

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