Water → 77586-77-7

HRID 1865759Notes

Reaction equation

HRID 1865759 reaction equation
C[C:2]([OH:15])([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>[OH:15][CH:2]([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]

Participants

6

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 69018721HCID 69018721, compound

Product 1

HCID 1127556977586-77-7

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
62.5 °C

Procedure

According to general procedure, methyl 2-hydroxy-3-methyl-3-phenylbutanoic acid (0.27 g, 1.3 mmol, from Reference Example 37) is dissolved in methanol (6 mL) and tetrahydrofuran (6 mL). To this solution is added water (3 mL) and lithium hydroxide monohydrate (0.12 g, 2.9 mmol), and the resulting mixture is stirred at 60-65° 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 2 M 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 pink oil, which solidified under vacuum (0.25 g, 100%). TOF MS (ES−): (M−H)=193.0

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 pink oil, which

Sources & evidence

ORD record
ord-088c2eb01ccf4eab9fc667f0979cfdd3
Source dataset
uspto-grants-2009_12
Patent number
US07626023B2

Reaction notes

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