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

HRID 985046Notes

Reaction equation

HRID 985046 reaction equation
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

Participants

7

Reactant 4

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

Product 1

HCID 225550394-[[4-[(4-Trifluoromethylphenoxy)methyl]phenyl]sulfanyl]-2-methylphenoxy-acetic acidYield 86.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-84be025bcd724916aa08fba89401046a
Source dataset
uspto-grants-2005_03
Patent number
US06869975B2

Reaction notes

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