4-(2-Chloro-2-cyanoethyl)benzoic acid → 55584-01-5

HRID 1287957Notes

Reaction equation

HRID 1287957 reaction equation
Cl[CH:2]([C:13]#[N:14])[CH2:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1>[Zn].C(O)(=O)C>[C:13]([CH2:2][CH2:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)#[N:14]

Participants

4

Reactant 1

HCID 508886404-(2-Chloro-2-cyanoethyl)benzoic acid

Product 1

HCID 1987919655584-01-5

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

100 parts of zinc powder are gradually added to a solution of 209.5 parts of 4-(2-chloro-2-cyanoethyl) benzoic acid in 500 parts of glacial acetic acid. The temperature rises quickly up to reflux and is maintained for approximately 1 hour. The solution is filtered when hot so a to eliminate the insoluble matter, then the filtrate is diluted with 1000 parts of water and the precipitate formed is isolated. Thus 122 parts of 4-(2-cyanoethyl) benzoic acid are obtained. M.P.: 182° C.

Workup

  1. temperatureto reflux
  2. temperatureis maintained for approximately 1 hour
  3. filtrationThe solution is filtered when hot so
  4. additionthe filtrate is diluted with 1000 parts of water
  5. customthe precipitate formed
  6. customis isolated

Sources & evidence

ORD record
ord-fd18203542204cbcac75390e6de83719
Source dataset
uspto-grants-1976_10
Patent number
US03987027

Reaction notes

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