Potassium Cyanide → Methyl 4-(2-cyanoethyl)benzoate

HRID 583685Notes

Reaction equation

HRID 583685 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1.[C-:14]#[N:15].[K+]>CS(C)=O.CCOC(C)=O>[C:14]([CH2:2][CH2:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1)#[N:15]

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 10586287Methyl 4-(2-bromoethyl)benzoate

Product 1

HCID 13308299Methyl 4-(2-cyanoethyl)benzoate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Bromide 23-2 (0.52 g, 2.14 mmol) and KCN (167 mg, 2.57 mmol) were combined in 10 mL DMSO. After 20 h, at RT and 1.5 h at 70° the reaction mixture was diluted with EtOAc, washed with water, sat. NaHCO3, 10 % KHSO4 and brine, dried (MgSO4), and concentrated providing 23-3 as a yellow solid. Rf 0.23 (30% EtOAc/hexanes).

Workup

  1. washwashed with water, sat. NaHCO3, 10 % KHSO4 and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-620120dbb3de484e90309e142d411d4d
Source dataset
uspto-grants-1999_07
Patent number
US05929120

Reaction notes

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