Potassium Cyanide → 4-(Cyanomethyl)benzoic acid

HRID 1955803Notes

Reaction equation

HRID 1955803 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].[K+]>O.CCO>[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

4

Reactant 2

HCID 9032Potassium CyanideHCID 225994-(Bromomethyl)benzoic acid

Product 1

HCID 2708714-(Cyanomethyl)benzoic acidYield 78.6%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A suspension of 4-bromomethylbenzoic acid (25.26 g, 0.12 mol) and KCN (20 g, 0.31 mol) in 5:7 H2O/EtOH (60 mL) was heated to 75°-80° C. for four hours. The cooled reaction was partially concentrated, H2O added, and extracted 1× with EtOAc. After acidification of the aqueous layer, the resulting precipitate was filtered and washed well with H2O to yield 13.6 g; 4 EtOAc extractions of the filtrate yielded an additional 2.7 g. Recrystallization of the combined solids from H2O/EtOH using activated charcoal and filtering through Celite afforded 15.20 g of 4-cyanomethylbenzoic acid.

Workup

  1. temperaturewas heated to 75°-80° C. for four hours
  2. customThe cooled reaction
  3. concentrationwas partially concentrated
  4. additionH2O added
  5. extractionextracted 1× with EtOAc
  6. filtrationAfter acidification of the aqueous layer, the resulting precipitate was filtered
  7. washwashed well with H2O
  8. customto yield 13.6 g
  9. extraction4 EtOAc extractions of the filtrate
  10. customyielded an additional 2.7 g
  11. customRecrystallization of the combined solids from H2O/EtOH using activated charcoal
  12. filtrationfiltering through Celite

Sources & evidence

ORD record
ord-33f3091e45834a6a93cca5ffdc39a28c
Source dataset
uspto-grants-1998_07
Patent number
US05776983

Reaction notes

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