Hydrochloric Acid → 1-[4-(Trifluoromethoxy)phenyl]cyclopropane-1-carboxylic acid

HRID 1666694Notes

Reaction equation

NN1CCCC1.[F:7][C:8]([F:23])([F:22])[O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2([C:19](N)=[O:20])[CH2:18][CH2:17]2)=[CH:12][CH:11]=1.[OH-:24].[Na+].Cl>CO>[F:7][C:8]([F:23])([F:22])[O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2([C:19]([OH:24])=[O:20])[CH2:18][CH2:17]2)=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 78 °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

waitThe reaction mixture was left stand
temperaturefor cooling
concentrationconcentrated under reduced pressure
filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record: ord-bd54535b29eb4a03a597ddecc8df4e78
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044068B2

Reaction notes

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