Hydrochloric Acid → 3-(3-Benzyl-4-hydroxy-phenyl)-2-ethoxy-propionic acid

HRID 709468Notes

Reaction equation

HRID 709468 reaction equation
C([O:3][C:4](=[O:24])[CH:5]([O:21][CH2:22][CH3:23])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:8]=1)C.[OH-].[K+].Cl>CO.O>[CH2:14]([C:9]1[CH:8]=[C:7]([CH2:6][CH:5]([O:21][CH2:22][CH3:23])[C:4]([OH:24])=[O:3])[CH:12]=[CH:11][C:10]=1[OH:13])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 22708450Ethyl 3-(3-benzyl-4-hydroxyphenyl)-2-ethoxypropanoate

Product 1

HCID 668649833-(3-Benzyl-4-hydroxy-phenyl)-2-ethoxy-propionic acidYield 100.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3-(3-benzyl-4-hydroxy-phenyl)-2-ethoxy-propionic acid ethyl ester (0.38 g, 1.16 mmol) in MeOH (5 mL), a solution of KOH (1.62 g, 29 mmol) in H2O (5 mL) was added. The mixture was stirred for 2 h at room temperature then acidified with aq. HCl (10%) and extracted with dichloromethane. The combined organic layers were dried and evaporated and the remaining crude product was purified by column chromatography to yield the title compound as an oil (0.35 g, 74.8%). Mass Spectrum: M+H+ 300.94, M−H+ 298.99.

Workup

  1. extractionextracted with dichloromethane
  2. customThe combined organic layers were dried
  3. customevaporated
  4. customthe remaining crude product was purified by column chromatography

Sources & evidence

ORD record
ord-68e0bf9b7b40421e859d1ba6ee98eacb
Source dataset
uspto-grants-2015_11
Patent number
US09181181B2

Reaction notes

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