Sodium Cyanide → (3-Benzoylphenyl)ethanenitrile

HRID 1759416Notes

Reaction equation

Br[CH2:2][C:3]1[CH:4]=[C:5]([C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:7][CH:8]=1.[C-:17]#[N:18].[Na+]>>[C:9]([C:5]1[CH:4]=[C:3]([CH2:2][C:17]#[N:18])[CH:8]=[CH:7][CH:6]=1)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

Reactant 2

HCID 8929Sodium Cyanide

HCID 895863-(Bromomethyl)benzophenone

Product 1

HCID 88857(3-Benzoylphenyl)ethanenitrile

Procedure

m-(Bromomethyl)benzophenone is reacted with sodium cyanide to form (m-benzoylphenyl)acetonitrile which is reacted with diethyl carbonate in the presence of sodium ethoxide to form sodium salt of ethyl alpha-cyano(m-benzoylphenyl)acetate. The sodium salt is reacted with methyl iodide to obtain ethyl alpha-cyano-alpha-(m-benzoylphenyl)propionate. The resulting ester is hydrolyzed and then subjected to decarboxylation to form alpha-(m-benzoylphenyl)propionitrile. Alkaline hydrolysis of alpha-(m-benzoylphenyl)propionitrile affords alpha-(m-benzoylphenyl)propionic acid. (For details, see British Patent No. 1,164,585).

Sources & evidence

ORD record: ord-87da0b0abb8243b7b31816804e20c489
Source dataset: uspto-grants-1982_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04340740

Reaction notes

Loading…