Hydrochloric Acid → 4-[1-(4'-Trifluoromethyl-biphenyl-4-ylmethyl)-propoxy]-benzoic acid

HRID 1669291Notes

Reaction equation

HRID 1669291 reaction equation
C[O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=3)=[CH:17][CH:16]=2)[CH2:12][CH3:13])=[CH:6][CH:5]=1.[OH-].[Na+].Cl>C(O)C>[F:28][C:27]([F:29])([F:30])[C:24]1[CH:23]=[CH:22][C:21]([C:18]2[CH:17]=[CH:16][C:15]([CH2:14][CH:11]([O:10][C:7]3[CH:6]=[CH:5][C:4]([C:3]([OH:31])=[O:2])=[CH:9][CH:8]=3)[CH2:12][CH3:13])=[CH:20][CH:19]=2)=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 673425784-[1-(4'-Trifluoromethyl-biphenyl-4-ylmethyl)-propoxy]-benzoic acid methyl ester

Product 1

HCID 673415704-[1-(4'-Trifluoromethyl-biphenyl-4-ylmethyl)-propoxy]-benzoic acidYield 90.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-[1-(4′-trifluoromethyl-biphenyl-4-ylmethyl)-propoxy]-benzoic acid methyl ester (0.048 g, 0.11 mmol) in ethanol (3 mL) is added sodium hydroxide (5.0N, 0.11 mL, 0.54 mmol) and stirred for four hours, acidified with 1.0 N HCl and extracted ethyl acetate three times. Organic layers are dried with sodium sulfate, filtered and concentrated under reduced pressure to provide 0.04 g (0.1 mmol, 89%) of title compound.

Workup

  1. extractionextracted ethyl acetate three times
  2. dry with materialOrganic layers are dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ced335933fb44e9dbc37fe6a573ce282
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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