Methanol → 4-[[4-[(4-Trifluoromethylphenoxy)methyl]phenyl]sulfanyl]-2-methylphenoxy-acetic acid

HRID 985046Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 985046
C([O:3][C:4](=[O:33])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][O:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=3)=[CH:16][CH:15]=2)=[CH:9][C:8]=1[CH3:32])C.C1COCC1.CO.[OH-].[Na+]>CCOC(C)=O.Cl>[F:30][C:28]([F:29])([F:31])[C:25]1[CH:26]=[CH:27][C:22]([O:21][CH2:20][C:17]2[CH:18]=[CH:19][C:14]([S:13][C:10]3[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]([OH:33])=[O:3])=[C:8]([CH3:32])[CH:9]=3)=[CH:15][CH:16]=2)=[CH:23][CH:24]=1

Komponenten

7

Edukt 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 207681104-[[4-[(4-Trifluoromethylphenoxy)methyl]phenyl]sulfanyl]-2-methylphenoxy-acetic acid ethyl ester

Produkt 1

HCID 225550394-[[4-[(4-Trifluoromethylphenoxy)methyl]phenyl]sulfanyl]-2-methylphenoxy-acetic acidAusbeute 86,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A 1 L round-bottomed flask was charged with compound 7.4 (40.9 g, 85.8 mmol), THF (100 mL) and MeOH (100 mL). Next, 2 N NaOH (86 mL, 172 mmol) was added dropwise, and the reaction was stirred at room temperature for 1 h. The solution was neutralized with 2 N HCl (86 mL) and the organic solvent was evaporated to give an aqueous solution and an insoluble oil. The residue was diluted with AcOEt (300 mL) and 1N HCl (300 mL), and partitioned. The organic phase was successively washed with water (400 mL) and brine (400 mL), dried over MgSO4, and concentrated to give white crystals. Recrystallization from 520 mL of AcOEt/hexane (3/10) gave compound 7 (33.4 g) as white crystals. MS APSI m/e: 447 (M−H). 1H NMR (400 MHz) (DMSO-d6) δ 13.0 (1H, brs); 7.64 (2H, d, J=8.8 Hz); 7.38 (2H, d, J=8.3 Hz); 7.30-7.20 (2H, m); 7.16 (4H, d, J=8.3 Hz); 6.89 (1H, d, J=8.5 Hz); 5.14 (2H, s); 4.74 (2H, s); 2.19 (3H, s).

Aufarbeitung

  1. customthe organic solvent was evaporated
  2. customto give an aqueous solution
  3. custompartitioned
  4. washThe organic phase was successively washed with water (400 mL) and brine (400 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customto give white crystals
  8. customRecrystallization from 520 mL of AcOEt/hexane (3/10)

Quellen und Nachweise

ORD-Eintrag
ord-84be025bcd724916aa08fba89401046a
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06869975B2

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