Sodium Hydroxide → 3-(1-(4-Fluorophenyl)cyclohexyl)propanoic acid

HRID 1506380Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of ethyl 3-(1-(4-fluorophenyl)cyclohexyl)propanoate (Intermediate 7, 1.347 g, 4.84 mmol) in methanol (20 mL) was added 1N sodium hydroxide (9.68 mL, 9.68 mmol), and the mixture was stirred at 60° C. for 7 hrs. After cooling, methanol was evaporated off and the residue was acidified with 12 mL of 1N HCl. The product was extracted with ethyl acetate (2×) and the combined extracts were washed with brine, dried over sodium sulfate and evaporated to give the desired 3-(1-(4-fluorophenyl)cyclohexyl)propanoic acid (1.183 g, 4.73 mmol, 98% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.26 (2H, dd, J=8.80, 5.28 Hz), 7.01 (2H, t, J=8.69 Hz), 2.01-2.10 (2H, m), 1.95-2.01 (2H, m), 1.82-1.88 (2H, m), 1.31-1.62 (8H, m).

Workup

temperatureAfter cooling
custommethanol was evaporated off
extractionThe product was extracted with ethyl acetate (2×)
washthe combined extracts were washed with brine
dry with materialdried over sodium sulfate
customevaporated

Sources & evidence

ORD record: ord-1daeaf4a8a604a9a93e3cf875d8ebac3
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216972B2

Reaction notes

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