Acetone Cyanohydrin → Methyl 3-(cyanomethyl)benzoate

HRID 1351409Notes

Reaction equation

HRID 1351409 reaction equation
C[N:2]([CH3:8])C(N(C)C)=N.Br[CH2:10][C:11]1[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=1)[C:14]([O:16][CH3:17])=[O:15].CC(C)(O)C#N>C(#N)C>[CH3:17][O:16][C:14](=[O:15])[C:13]1[CH:18]=[CH:19][CH:20]=[C:11]([CH2:10][C:8]#[N:2])[CH:12]=1

Participants

5

Reactant 3

HCID 6406Acetone CyanohydrinHCID 664601,1,3,3-TetramethylguanidineHCID 517981Methyl 3-(bromomethyl)benzoate

Product 1

HCID 10821136Methyl 3-(cyanomethyl)benzoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1,1,3,3-Tetramethylguanidine (3.21 ml, 25.6 mmol) was added dropwise to a solution of methyl 3-bromomethylbenzoate (2.80 g, 12.2 mmol) and acetone cyanohydrin (1.59 ml, 18.3 mmol) in acetonitrile (40 ml) at room temperature. The reaction was stirred for 3 days and the solvent then removed under reduced pressure. The resulting brown oil was purified by column chromatography on silica gel using ethyl acetate:pentane (50:50) as eluant to afford the title compound as a clear oil, 1.80 g.

Workup

  1. customthe solvent then removed under reduced pressure
  2. customThe resulting brown oil was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-12fbbf405903469db1936e3ff5d5e927
Source dataset
uspto-grants-2007_05
Patent number
US07217714B1

Reaction notes

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