Sodium Hydroxide → {[2-Methyl-4-({1-[4'-(trifluoromethyl)-4-biphenylyl]pentyl}oxy)phenyl]oxy}acetic acid

HRID 1391809Notes

Reaction equation

HRID 1391809 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH:9]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=3)=[CH:16][CH:15]=2)[CH2:10][CH2:11][CH2:12][CH3:13])[CH:5]=[CH:4][C:3]=1[O:30][CH2:31][C:32]([O:34]CC)=[O:33].[OH-].[Na+]>O1CCOCC1.O>[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH:9]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:27])([F:28])[F:29])=[CH:22][CH:21]=3)=[CH:16][CH:15]=2)[CH2:10][CH2:11][CH2:12][CH3:13])[CH:5]=[CH:4][C:3]=1[O:30][CH2:31][C:32]([OH:34])=[O:33]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86604657Ethyl {[2-methyl-4-({1-[4'-(trifluoromethyl)-4-biphenylyl]pentyl}oxy)phenyl]oxy}acetate

Product 1

HCID 10073534{[2-Methyl-4-({1-[4'-(trifluoromethyl)-4-biphenylyl]pentyl}oxy)phenyl]oxy}acetic acidYield 85.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of ethyl {[2-methyl-4-({1-[4′-(trifluoromethyl)-4-biphenylyl]pentyl}oxy)phenyl]oxy}acetate (310 mg, 0.62 mmol) in dioxan (6 mL) and water (3 mL), was added aqueous NaOH (2M, 2.43 mL, 1.22 mmol), and the mixture stirred at rt for 1 hour. The dioxan was removed under vacuum and brine (5 mL) added to the residue. The precipitate was collected by filtration and dried under vacuum to give the title compound as a white solid (250 mg).

Workup

  1. customThe dioxan was removed under vacuum and brine (5 mL)
  2. additionadded to the residue
  3. filtrationThe precipitate was collected by filtration
  4. customdried under vacuum

Sources & evidence

ORD record
ord-f2b38a30046747fba6f3f67e48ad2c7a
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

Loading…