Hydrogen Peroxide → HCID 57970159, compound

HRID 1666693Notes

Reaction equation

HRID 1666693 reaction equation
[F:1][C:2]([F:16])([F:15])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:13]#[N:14])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1.[OH-:17].[Na+].OO>CO>[F:1][C:2]([F:15])([F:16])[O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2([C:13]([NH2:14])=[O:17])[CH2:11][CH2:12]2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 459257331-[4-(Trifluoromethoxy)phenyl]cyclopropane-1-carbonitrile

Product 1

HCID 57970159HCID 57970159, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 1-(4-trifluoromethoxyphenyl)cyclopropanecarbonitrile (4.0 g), 25% aqueous sodium hydroxide (0.46 mL), 30% aqueous hydrogen peroxide (25 mL), and methanol (100 mL) was heated at 55° C. for 1 h with stirring. The reaction mixture was concentrated under reduced pressure, the precipitated crystals were collected by filtration, to obtain white solid 1-(4-(trifluoromethoxy)phenyl)cyclopropanecarbamide (4.5 g). (3) A mixture of 1-(4-trifluoromethoxyphenyl)cyclopropanecarbamide (4.5 g), 15% aqueous sodium hydroxide (150 mL), and methanol (60 mL) was heated at 78° C. for 18 h with stirring. The reaction mixture was left stand for cooling, then the reaction solution was adjusted to pH 2 using 15% hydrochloric acid and concentrated under reduced pressure. The precipitated crystals were collected by filtration to obtain white solid 1-(4-(trifluoromethoxy)phenyl)cyclopropanecarboxylic acid (4.5 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-90e03dc305b2483b8b070ed68562d48c
Source dataset
uspto-grants-2011_10
Patent number
US08044068B2

Reaction notes

Loading…