Lithium hydroxide, monohydrate → 3-Cyclopropyl-3-methylbutanoic acid

HRID 1927657Notes

Reaction equation

HRID 1927657 reaction equation
C([O:3][C:4](=[O:12])[CH2:5][C:6]([CH:9]1[CH2:11][CH2:10]1)([CH3:8])[CH3:7])C.O.[OH-].[Li+]>C1COCC1.O.CO.O>[CH:9]1([C:6]([CH3:8])([CH3:7])[CH2:5][C:4]([OH:12])=[O:3])[CH2:11][CH2:10]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 267154Ethyl 3-cyclopropyl-3-methylbutanoate

Product 1

HCID 553033053-Cyclopropyl-3-methylbutanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A mixture of 3-cyclopropyl-3-methylbutyric acid ethyl ester (3.0 g, 17.6 mmol) and lithium hydroxide monohydrate (3.5 g, 105 mmol) in THF/H2O/MeOH (24 mL, 2:1:1 v/v) was stirred at rt overnight. The reaction mixture was diluted with water (100 mL), and washed with ethyl acetate (2×50 mL). The aqueous layer was acidified with 2M HCl and extracted with ethyl acetate (3×100 mL). The combined organic extracts were washed with brine (200 mL), dried over sodium sulfate and concentrated to give 3-cyclopropyl-3-methylbutyric acid.

Workup

  1. washwashed with ethyl acetate (2×50 mL)
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. washThe combined organic extracts were washed with brine (200 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-93a775fc23a24cec9043a868134050d6
Source dataset
uspto-grants-2012_05
Patent number
US08183275B2

Reaction notes

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