Hydrochloric Acid → 1-[3,5-Bis(trifluoromethyl)phenyl]cyclopropanecarboxylic acid

HRID 2047445Notes

Reaction equation

[F:1][C:2]([F:21])([F:20])[C:3]1[CH:4]=[C:5]([C:13]2([C:16]([O:18]C)=[O:17])[CH2:15][CH2:14]2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[OH-].[Na+].Cl>CO>[F:1][C:2]([F:20])([F:21])[C:3]1[CH:4]=[C:5]([C:13]2([C:16]([OH:18])=[O:17])[CH2:15][CH2:14]2)[CH:6]=[C:7]([C:9]([F:11])([F:12])[F:10])[CH:8]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of the compound (1.80 g) obtained in step 2 in methanol (10 mL) was added 8N aqueous sodium hydroxide solution (10 mL), and the mixture was stirred at 60° C. for 1.5 hr. The reaction mixture was cooled, and the mixture was acidified with 6N hydrochloric acid, and methanol was evaporated under reduced pressure. The residue was extracted twice with ethyl acetate, dried and concentrated under reduced pressure to give the title compound (1.39 g, 81%) as a white powder.

Workup

temperatureThe reaction mixture was cooled
customwas evaporated under reduced pressure
extractionThe residue was extracted twice with ethyl acetate
customdried
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-2ab5f1f22a8540adb4977d1f9ea2ebee
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592454B2

Reaction notes

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