Sodium Hydroxide → 4-(3,5-Bis(trifluoromethyl)benzyloxy)-3-phenylbutanoic acid

HRID 548198Notes

Reaction equation

HRID 548198 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:4]=[C:5]([CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:24]=1)[CH2:6][O:7][CH2:8][CH:9]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:10][C:11]([O:13]CC)=[O:12].[OH-].[Na+]>C(O)C>[F:1][C:2]([F:29])([F:30])[C:3]1[CH:4]=[C:5]([CH:22]=[C:23]([C:25]([F:27])([F:26])[F:28])[CH:24]=1)[CH2:6][O:7][CH2:8][CH:9]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:10][C:11]([OH:13])=[O:12]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86624037Ethyl 4-(3,5-bis(trifluoromethyl)benzyloxy)-3-phenylbutanoate

Product 1

HCID 866240384-(3,5-Bis(trifluoromethyl)benzyloxy)-3-phenylbutanoic acidYield 109.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 4-(3,5-bis(trifluoromethyl)benzyloxy)-3-phenylbutanoate (26.06 g, 60 mmol) was dissolved in ethanol (300 mL), a 2 mol/L aqueous solution of sodium hydroxide was added thereto and the mixture was stirred for 20 hours at room temperature. The solvent was evaporated in vacuo and the resulting residue was dissolved in water and acidified with 6 mol/L hydrochloric acid. The oily product separated out therefrom was extracted with chloroform and the organic layers were combined and washed with water and a saturated saline solution. After it was dried over anhydrous sodium sulfate, the solvent was evaporated in vacuo to give 4-(3,5-bis(trifluoromethyl)benzyloxy)-3-phenylbutanoic acid (26.60 g, 90%) as an oily product. 1H-NMR (DMSO-d6) δ: 2.56 (dd, J=8.4, 16.0 Hz, 1H), 2.73 (dd, J=6.4, 16.0 Hz, 1H), 3.35-3.40 (m, 1H), 3.63-3.66 (m, 2H), 4.64 and 4.66 (ABq, J=13.4 Hz, 2H), 7.19-7.25 (m, 1H), 7.27-7.31 (m, 4H), 7.88 (s, 2H), 7.98 (s, 1H), 12.09 (brs, 1H).

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionthe resulting residue was dissolved in water
  3. customThe oily product separated out
  4. extractiontherefrom was extracted with chloroform
  5. washwashed with water
  6. dry with materialAfter it was dried over anhydrous sodium sulfate
  7. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-15bd7307ac574a6c814ce9446a0d1a27
Source dataset
uspto-grants-2011_05
Patent number
US07939552B2

Reaction notes

Loading…