Potassium Hydroxide → 3-(2-Chloro-4-cyanophenyl)propanoic acid

HRID 68027Notes

Reaction equation

HRID 68027 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][C:3]=1[CH2:10][CH2:11][C:12]([O:14]CC)=[O:13].[OH-].[K+]>C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][C:3]=1[CH2:10][CH2:11][C:12]([OH:14])=[O:13]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 13042095Ethyl 3-(chloro-4-cyanophenyl)propanoate

Product 1

HCID 130420963-(2-Chloro-4-cyanophenyl)propanoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of ethyl 3-(chloro-4-cyanophenyl)propanoate (33.0 g, 0.14 mol), KOH (6.27 g, 0.11 mol) and 95% ethanol (109 mL) was warmed at 40° C. for 1 h. The mixture was neutralized and evaporated to dryness. The residue was dissolved in 5% NaHCO3 and washed with EtOAc. Acidification and filtration gave crystalline 3-(2-chloro-4-cyanophenyl) propanoic acid: 18.4 g; mp 127°-219° C.

Workup

  1. customevaporated to dryness
  2. dissolutionThe residue was dissolved in 5% NaHCO3
  3. washwashed with EtOAc
  4. filtrationAcidification and filtration

Sources & evidence

ORD record
ord-a8ff8187a948457790302e84f15453e1
Source dataset
uspto-grants-1982_08
Patent number
US04347382

Reaction notes

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