Potassium Hydroxide → 4-(Aminocarbonyl)benzeneacetic acid

HRID 1722418Notes

Reaction equation

HRID 1722418 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([O:12]CC)=[O:11])=[CH:5][CH:4]=1)#[N:2].[OH-:15].[K+]>CC(O)(C)C.[Na+].[Cl-]>[NH2:2][C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1)=[O:15]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 279718Ethyl 2-(4-cyanophenyl)acetate

Product 1

HCID 141809504-(Aminocarbonyl)benzeneacetic acid

Reagents, catalysts & solvents 2

HCID 5234Sodium ChlorideSolventHCID 6386tert-ButanolSolvent

Procedure

A mixture of ethyl 4-cyanobenzeneacetate (1.9 g) and freshly ground KOH (2.8 g) in 2-methylpropan-2-ol (20 ml) was heated under gentle reflux for 20 min. The resulting mixture was cooled, diluted with 50% saturated NaCl solution (50 ml), washed with CHCl3 (4×50 ml), and acidified with 2M hydrochloric acid (25 ml) to precipitate the title compound (1.65 g) as a fine white solid m.p. 226°-227°.

Workup

  1. temperaturewas heated
  2. temperatureunder gentle reflux for 20 min
  3. temperatureThe resulting mixture was cooled
  4. washwashed with CHCl3 (4×50 ml)
  5. customto precipitate the title compound (1.65 g) as a fine white solid m.p. 226°-227°

Sources & evidence

ORD record
ord-9bfbdf1916454db791a95e92244874ee
Source dataset
uspto-grants-1989_08
Patent number
US04855314

Reaction notes

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