Sodium Cyanide → 4-(Cyanomethyl)benzoic acid

HRID 966775Notes

Reaction equation

HRID 966775 reaction equation
Br[CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.[C-:12]#[N:13].[Na+].[OH-].[Na+]>C(#N)C.O>[C:12]([CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)#[N:13]

Participants

6

Reactant 3

HCID 8929Sodium CyanideHCID 14798Sodium HydroxideHCID 225994-(Bromomethyl)benzoic acid

Product 1

HCID 2708714-(Cyanomethyl)benzoic acidYield 26.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 4-bromomethyl-benzoic acid (4.0 g, 18.6 mmol) in acetonitrile (186 mL) was treated with a solution of sodium cyanide (1.0 g, 20.4 mmol) and sodium hydroxide (0.74 g, 18.6 mmol) in water (24 mL). The reaction mixture was heated at reflux for 2 h. At this time, the reaction was cooled to 25° C. and concentrated in vacuo. The resulting solution was washed with chloroform (1×50 mL). The aqueous layer was acidified to pH=3 with a 1N aqueous hydrochloric acid solution. The aqueous layer was extracted with a solution of chloroform/methanol (9:1, 3×100 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to afford 4-cyanomethyl-benzoic acid (0.79 g, 26.3%) as a white solid: mp 193-195° C.; EI-HRMS m/e calcd for C9H7NO2 (M+) 161.0476, found 161.0483.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 h
  3. concentrationconcentrated in vacuo
  4. washThe resulting solution was washed with chloroform (1×50 mL)
  5. extractionThe aqueous layer was extracted with a solution of chloroform/methanol (9:1, 3×100 mL)
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-410a900b76dd4260b545a1da929d681a
Source dataset
uspto-grants-2005_10
Patent number
US06951945B2

Reaction notes

Loading…