Hydrochloric Acid → 2-(4-(Benzyloxy)-3-methylphenyl)-2-ethylbutanoic acid

HRID 1486520Notes

Reaction equation

HRID 1486520 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([CH2:22][CH3:23])([CH2:20][CH3:21])[C:16]([O:18]C)=[O:17])=[CH:11][C:10]=1[CH3:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO.O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([CH2:22][CH3:23])([CH2:20][CH3:21])[C:16]([OH:18])=[O:17])=[CH:11][C:10]=1[CH3:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 591667152-(4-Benzyloxy-3-methyl-phenyl)-2-ethyl-butyric acid methyl ester

Product 1

HCID 591667042-(4-(Benzyloxy)-3-methylphenyl)-2-ethylbutanoic acidYield 91.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of compound 18 (220 mg, 0.674 mmol) in 5 ml of MeOH was added 5 ml of 20% NaOH solution in water and refluxed for 48 h. Reaction mixture is acidified to pH 1 with 1 M HCl solution and extracted with EtOAc (3×5 ml), the combined organic layers were washed with H2O and dried with Na2SO4. The solution was concentrated in vacuo to give compound 19 192 mg in 91% yield. Rf=0.10 (20% EtOAc/Hexane);

Workup

  1. temperaturerefluxed for 48 h
  2. customReaction mixture
  3. extractionextracted with EtOAc (3×5 ml)
  4. washthe combined organic layers were washed with H2O
  5. dry with materialdried with Na2SO4
  6. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-2a2c4c36094d4bbc99655b42f7ce0e47
Source dataset
uspto-grants-2016_08
Patent number
US09428447B2

Reaction notes

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