Water → (5-Benzyloxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid

HRID 426358Notes

Reaction equation

HRID 426358 reaction equation
C([O:3][C:4](=[O:30])[CH2:5][C:6]1[CH:7]=[C:8]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)[CH:9]=[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]=1)C.O.O[Li].O>C1COCC1>[CH2:13]([O:12][C:10]1[CH:11]=[C:6]([CH2:5][C:4]([OH:30])=[O:3])[CH:7]=[C:8]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:28])([F:29])[F:27])=[CH:22][CH:21]=2)[CH:9]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 24771790Ethyl [5-benzyloxy-4'-(trifluoromethyl)biphenyl-3-yl]acetate

Product 1

HCID 11501912(5-Benzyloxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acidYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (5-benzyloxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester (120 g, 0.29 mol) in THF (1.2 L) was added water (240 mL), LiOH.H2O (16 g, 0.32 mol) and stirred at room temperature for 16 h. The solution was filtered and concentrated in vacuo to remove THF. The resulting thick liquid was acidified to pH 2 by adding 2N aqueous HCl solution and the white suspension was mechanically stirred for 1 h at room temperature. The wet white product was recovered after filtration and dissolved in EtOAc (500 mL). The organic layer was separated from water, dried (MgSO4) and concentrated in vacuo to obtain (5-benzyloxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid (105 g, 94%).

Workup

  1. filtrationThe solution was filtered
  2. concentrationconcentrated in vacuo
  3. customto remove THF
  4. additionby adding 2N aqueous HCl solution
  5. stirringthe white suspension was mechanically stirred for 1 h at room temperature
  6. customThe wet white product was recovered
  7. filtrationafter filtration
  8. dissolutiondissolved in EtOAc (500 mL)
  9. customThe organic layer was separated from water
  10. dry with materialdried (MgSO4)
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c8a8114657224298a2ce85601994e086
Source dataset
uspto-grants-2012_01
Patent number
US08106236B2

Reaction notes

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