Hydrochloric Acid → 4-[[2-Chloro-4-[(4-trifluoromethylphenoxy)methyl]phenyl]sulfanyl]-2-methylphenoxy-acetic acid

HRID 985053Notes

Reaction equation

HRID 985053 reaction equation
C([O:3][C:4](=[O:34])[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][C:15]=2[Cl:32])=[CH:9][C:8]=1[CH3:33])C.[OH-].[Na+].Cl>CCO>[Cl:32][C:15]1[CH:16]=[C:17]([CH2:20][O:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:30])([F:29])[F:31])=[CH:24][CH:23]=2)[CH:18]=[CH:19][C:14]=1[S:13][C:10]1[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]([OH:34])=[O:3])=[C:8]([CH3:33])[CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 207681144-[[2-Chloro-4-[(4-trifluoromethylphenoxy)methyl]phenyl]sulfanyl]-2-methylphenoxy-acetic acid ethyl ester

Product 1

HCID 101168424-[[2-Chloro-4-[(4-trifluoromethylphenoxy)methyl]phenyl]sulfanyl]-2-methylphenoxy-acetic acidYield 75.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 1 L round-bottomed flask was charged with compound 10.6 (43.4 g, 84.9 mmol) and EtOH (386 mL). Next, 4 N NaOH (42 mL, 168 mmol) was added dropwise, and the reaction was stirred at room temperature for 30 min. The reaction was then neutralized using 343 mL of 0.5 N HCl, deposited crystals were collected, washed with 2×100 mL of water, and dried in vacuo. Recrystallization from 508 mL of AcOEt/hexanes ({fraction (2/8)}) furnished the title compound 10 (31.1 g) as white crystals. MS APSI m/e: 481 (M−H). 1H NMR (400 MHz) (DMSO-d6) δ 12.98 (1H, brs); 7.65 (2H, d, J=8.7 Hz); 7.58 (1H, s); 7.36-7.29 (3H, m); 7.17 (2H, d, J=8.6 Hz); 6.96 (1H, d, J=8.4 Hz); 6.74 (1H, d, J=8.2 Hz); 5.14 (2H, s); 4.77 (2H, s); 2.21 (3H, s).

Workup

  1. customwere collected
  2. washwashed with 2×100 mL of water
  3. customdried in vacuo
  4. customRecrystallization from 508 mL of AcOEt/hexanes ({fraction (2/8)})

Sources & evidence

ORD record
ord-84232a865cc44d7db7df288c66211fd4
Source dataset
uspto-grants-2005_03
Patent number
US06869975B2

Reaction notes

Loading…