Hydrochloric Acid → HCID 22279992, compound

HRID 1063676Notes

Reaction equation

HRID 1063676 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=3)=[CH:17][CH:16]=2)=[CH:8][C:7]=1[CH3:31].O.[OH-].[Li+].Cl>O1CCCC1.O>[CH3:31][C:7]1[CH:8]=[C:9]([S:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:22]=[CH:23][C:24]([C:27]([F:29])([F:28])[F:30])=[CH:25][CH:26]=3)=[CH:17][CH:16]=2)[CH:10]=[CH:11][C:6]=1[O:5][CH2:4][C:3]([OH:32])=[O:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 20827004HCID 20827004, compound

Product 1

HCID 22279992HCID 22279992, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of {2-methyl-4-[2-(4′-trifluoromethyl-biphenyl-4-yl)-ethylsulfanyl]-phenoxy}-acetic acid methyl ester (0.78 g, 1.7 mmol) in 10 ml of tetrahydrofuran and 2.0 ml of water was treated with lithium hydroxide monohydrate (0.21 g, 5.0 mmol), and the mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with 5.0 ml of water and made strongly acidic by the addition of 4.0 N hydrochloric acid. The mixture was extracted with ethyl acetate (4×30 ml), and the combined extracts were washed with brine (2×50 ml), then dried over anhydrous sodium sulfate and concentrated. The crude product was recrystallized from ethyl acetate/hexane. mp 132-134° C.; IR (thin film) cm−1: 1741, 1709, 1490, 1326, 1239, 1110; 400 MHz 1H NMR (DMSO-d6) δ 7.82 (d, 2H, J=8.0 Hz), 7.74 (d, 2H, J=8.0 Hz), 7.61 (d, 2H, J=8.3 Hz), 7.31 (d, 2H, J=8.3 Hz), 7.15 (m, 2H), 6.75 (d, 1H, J=8.3 Hz), 4.64 (s, 2H), 3.11 (t, 2H, J=7.6 Hz), 2.82 (t, 2H, J=7.6 Hz), 2.12 (s, 3H); MS m/z 447 (M+1). Anal. Calc'd for C24H21F3O3S: C, 64.56; H, 4.74. found: C, 64.45; H, 4.58.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (4×30 ml)
  2. washthe combined extracts were washed with brine (2×50 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe crude product was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-7cc9b46a1caf4075833370d24f81c912
Source dataset
uspto-grants-2005_11
Patent number
US06964983B2

Reaction notes

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