Potassium Hydroxide → 2-(Cyclobutylmethyl)malonic acid
Reaction equation
C([O:3][C:4](=[O:16])[CH:5]([CH2:11][CH:12]1[CH2:15][CH2:14][CH2:13]1)[C:6]([O:8]CC)=[O:7])C.[OH-].[K+]>C(O)C.O>[CH:12]1([CH2:11][CH:5]([C:6]([OH:8])=[O:7])[C:4]([OH:16])=[O:3])[CH2:15][CH2:14][CH2:13]1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 110 °C
Procedure
A solution of 2-cyclobutylmethyl-malonic acid diethyl ester (4.68 g, 20.5 mmol) in ethanol (45.4 mL) was treated with a solution of potassium hydroxide (3.45 g, 61.5 mmol) in water (11.4 mL). The reaction was then heated to 110° C. overnight. After this time, the reaction was cooled to 25° C. and was concentrated in vacuo. The residue was diluted with water (50 mL) which was then acidified with a 2N aqueous hydrochloric acid solution and then extracted with a 90/10 methylene chloride/methanol solution (3×50 mL). The combined organics were dried over sodium sulfate, filtered and concentrated in vacuo to afford 2-cyclobutylmethyl-malonic acid (1.22 g, 34.7%) as a tan solid. This material was used without further purification.
Workup
- temperatureAfter this time, the reaction was cooled to 25° C.
- concentrationwas concentrated in vacuo
- additionThe residue was diluted with water (50 mL) which
- extractionextracted with a 90/10 methylene chloride/methanol solution (3×50 mL)
- dry with materialThe combined organics were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-ff9c1d972e28423e99ee4c6549042bf5
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08258134B2
Reaction notes
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