Hydrochloric Acid → 2-[3-[4-(Trifluoromethyl)phenethyloxy]-4-methoxybenzyl]butyric acid

HRID 1826093Notes

Reaction equation

[CH2:1]([CH:3]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)[CH:11]=1)[C:4]([O:6]CC)=[O:5])[CH3:2].[OH-].[Na+].Cl>CO>[CH2:1]([CH:3]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH2:19][CH2:20][C:21]2[CH:22]=[CH:23][C:24]([C:27]([F:28])([F:29])[F:30])=[CH:25][CH:26]=2)[CH:11]=1)[C:4]([OH:6])=[O:5])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of ethyl 2-ethyl-3-[4-methoxy-3-[2-[4-(trifluoromethyl)phenyl]ethoxy]phenyl]propanoate (793 mg, 1.87 mmol), methanol (20 mL) and 1 mol/L aqueous solution of sodium hydroxide (10 mL) was stirred for 4 hours at 60° C. After cooling, ice water (50 mL) was added and the mixture was made acidic with 1 mol/L hydrochloric acid, which was then extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, and then concentrated. The residue was purified by silica gel column chromatography (eluent: n-hexane:ethyl acetate=4:1 v/v) to afford 654 mg (88%) of the title compound as colorless crystals. Further, these were recrystallized from diethyl ether-n-hexane, thus obtaining 391 mg of the purified title compound as colorless needles.

Workup

temperatureAfter cooling
extractionwas then extracted with ethyl acetate
washThe organic layer was washed with water and brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated
customThe residue was purified by silica gel column chromatography (eluent: n-hexane:ethyl acetate=4:1 v/v)

Sources & evidence

ORD record: ord-7b611c8b19654b2f8b1ba79db308bb75
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07049342B2

Reaction notes

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