Water → 1-(4-Bromophenyl)cyclopropane-1-carboxylic acid

HRID 45595Notes

Reaction equation

HRID 45595 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]#N)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[OH-:13].[K+].[OH2:15]>C(O)CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([OH:15])=[O:13])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 27952731-(4-Bromophenyl)Cyclopropanecarbonitrile

Product 1

HCID 162279661-(4-Bromophenyl)cyclopropane-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
180 °C

Procedure

1-(4-Bromo-phenyl)-cyclopropanecarbonitrile (5 g, 22.5 mmol) and potassium hydroxide (5 g, 89.3 mmol) were combined in ethylene glycol (70 mL), and the reaction was stirred at 180° C. for 4 hours. The mixture was poured into H2O, acidified, and filtered to give the title compound.

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-98ecc165e9fa444bb6cf22925aea77b3
Source dataset
uspto-grants-2013_09
Patent number
US08541587B2

Reaction notes

Loading…