2-(Cyclobutylmethyl)malonic acid → 3-Cyclobutylpropanoic acid
Reaction equation
[CH:1]1([CH2:5][CH:6](C(O)=O)[C:7]([OH:9])=[O:8])[CH2:4][CH2:3][CH2:2]1>C(Cl)Cl.CO>[CH:1]1([CH2:5][CH2:6][C:7]([OH:9])=[O:8])[CH2:4][CH2:3][CH2:2]1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
2-Cyclobutylmethyl-malonic acid (1.20 g, 6.9 mmol) was heated at 195° C. for 2 h. After this time, the resulting brown solution was cooled to 25° C. and diluted with a 90/10 methylene chloride/methanol solution (50 mL). The organics were then washed with a saturated aqueous sodium chloride solution, concentrated in vacuo and azeotroped with acetonitrile (2×10 mL) to afford 3-cyclobutyl-propionic acid (770 mg, 85%) as brown oil. The material was used without further purification.
Workup
- washThe organics were then washed with a saturated aqueous sodium chloride solution
- concentrationconcentrated in vacuo
- customazeotroped with acetonitrile (2×10 mL)
Sources & evidence
- ORD record
- ord-da7227ef9b154a60bbb9c03f0e38eafb
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08258134B2
Reaction notes
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