Water → HCID 11424320, compound

HRID 133850Notes

Reaction equation

HRID 133850 reaction equation
C[C:2]([O:15][CH3:16])([C:6]([CH3:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:7])[C:3]([OH:5])=[O:4].O.O.[OH-].[Li+]>CO.O1CCCC1>[CH3:16][O:15][CH:2]([C:6]([CH3:14])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH3:7])[C:3]([OH:5])=[O:4]

Participants

6

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 69018132HCID 69018132, compound

Product 1

HCID 11424320HCID 11424320, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

According to General Procedure II, methyl 2-methoxy-3-methyl-3-phenylbutanoic acid (0.49 g, 2.2 mmol, from Reference Example 38) is dissolved in methanol (10 mL) and tetrahydrofuran (10 mL). To this solution is added water (5 mL) and lithium hydroxide monohydrate (0.18 g, 4.4 mmol), and the resulting mixture is stirred at 60° C. for 16 hours. Solvents are removed in vacuo and the residue is then dissolved in water. The solution is acidified to pH 1 with 10% aqueous hydrochloric acid solution and then extracted thrice with ethyl acetate. The combined extracts are washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, decanted, and concentrated under reduced pressure to afford a light orange oil, which solidified to a straw colored crystalline solid (0.46 g, 100%). MS (ES−): (M−H)=207.0

Workup

  1. customSolvents are removed in vacuo
  2. dissolutionthe residue is then dissolved in water
  3. extractionextracted thrice with ethyl acetate
  4. washThe combined extracts are washed with saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customdecanted
  7. concentrationconcentrated under reduced pressure
  8. customto afford a light orange oil, which

Sources & evidence

ORD record
ord-da993784e34b4f36b9f05b62d77ad9b4
Source dataset
uspto-grants-2008_06
Patent number
US07390910B2

Reaction notes

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