Hydrochloric Acid → 4-(2-Methoxyphenyl)-3-methylbutanoic acid

HRID 514032Notes

Reaction equation

HRID 514032 reaction equation
C([O:3][C:4](=[O:17])[CH2:5][CH:6]([CH3:16])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][CH3:15])C.Cl>C1COCC1.CCO.[Li+].[OH-]>[CH3:15][O:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[CH2:7][CH:6]([CH3:16])[CH2:5][C:4]([OH:17])=[O:3]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 671261154-(2-Methoxyphenyl)-3-methyl-butyric acid ethyl ester

Product 1

HCID 239394044-(2-Methoxyphenyl)-3-methylbutanoic acid

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3939Lithium HydroxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(2-methoxyphenyl)-3-methyl-butyric acid ethyl ester (24 mmol, crude from previous reaction) in THF (50 mL), EtOH (50 mL) and LiOH (1 M, 50 mL) was stirred at room temperature overnight. The reaction was acidified with 1 M HCl, and extracted with EtOAc. The combined extracts were washed with brine and dried over sodium sulfate. Concentration gave the desired product, which was used without further purification. LCMS-ESI+ (m/z): [M]+ calcd for C12H16O3: 208.11. Found: 208.86

Workup

  1. extractionextracted with EtOAc
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationConcentration

Sources & evidence

ORD record
ord-9c1b4f8a779740b6a5760492bb351aee
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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