Hydrochloric Acid → 2-(3-Benzyloxy-5-trifluoromethyl-phenyl)propionic acid

HRID 563557Notes

Reaction equation

HRID 563557 reaction equation
C([O:3][C:4](=[O:25])[CH:5]([C:7]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:8]=1)[CH3:6])C.CO.[Li+].[OH-].Cl>O.C1COCC1>[CH2:18]([O:17][C:9]1[CH:8]=[C:7]([CH:5]([CH3:6])[C:4]([OH:25])=[O:3])[CH:12]=[C:11]([C:13]([F:15])([F:16])[F:14])[CH:10]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 574587982-(3-Benzyloxy-5-trifluoromethyl-phenyl)-propionic acid ethyl ester

Product 1

HCID 574587992-(3-Benzyloxy-5-trifluoromethyl-phenyl)propionic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-(3-Benzyloxy-5-trifluoromethyl-phenyl)-propionic acid ethyl ester (1.4 g, 4.0 mmol) in 2:2:1 MeOH:THF:H2O was treated with 1N aqueous LiOH (3 mL) at room temperature overnight. The mixture was acidified with 10% aqueous HCl and extracted three times with EtOAc. The combined organic layers were concentrated and purified by silica gel chromatography to give the title compound.

Workup

  1. extractionextracted three times with EtOAc
  2. concentrationThe combined organic layers were concentrated
  3. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-445bd6b2813b45b9a528311ebeb67fd9
Source dataset
uspto-grants-2011_11
Patent number
US08067445B2

Reaction notes

Loading…