Sodium Hydroxide → HCID 58083452, compound

HRID 2404331Notes

Reaction equation

[OH-].[Na+].[CH2:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:16]=[CH:15][C:14]([C:17]([O:19]C)=[O:18])=[CH:13][C:12]=1[C:21]([F:24])([F:23])[F:22])[CH3:4]>CCO>[CH2:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:16]=[CH:15][C:14]([C:17]([OH:19])=[O:18])=[CH:13][C:12]=1[C:21]([F:22])([F:23])[F:24])[CH3:4]

Participants

Conditions

Temperature: 60 °C

Procedure

A 5N aqueous solution of NaOH (3 mL, 15 mmol) was added into a solution of methyl 2′-ethyl-2-(trifluoromethyl)biphenyl-4-carboxylate (3.05 g, 9.89 mmol) in EtOH (30 mL) and the resulting mixture was heated at 60° C. for 45 minutes. The reaction mixture was concentrated under vacuum. The residue was taken up with water (50 mL) and a 5N aqueous solution of HCl (5 mL), and then extracted with MTBE (2×100 mL). The organic layers were washed with brine (50 mL), combined, dried (MgSO4) and the solvent was removed under reduced pressure to give the title compound as a white powder (2.71 g, 93%). HPLC (Method A) Rt 4.8 min (Purity: 97.3%). LC/MS (Method B): 293.1 (M−H)−. 1H NMR (DMSO-d6, 300 MHz) δ 13.54 (s, 1H), 8.29 (d, J=1.5 Hz, 1H), 8.22 (dd, J=7.9, 1.5 Hz, 1H), 7.50 (d, J=7.9 Hz, 1H), 7.42-7.32 (m, 2H), 7.24 (m, 1H), 7.10 (d, J=7.5 Hz, 1H), 2.39-2.13 (m, 2H), 1.00 (t, J=7.6 Hz, 3H).

Workup

concentrationThe reaction mixture was concentrated under vacuum
extractiona 5N aqueous solution of HCl (5 mL), and then extracted with MTBE (2×100 mL)
washThe organic layers were washed with brine (50 mL)
dry with materialdried (MgSO4)
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-14ff7dd9d3774f6685b24f8a112c65db
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802704B2

Reaction notes

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