Hydrochloric Acid → 2-(Methoxycarbonyl)cyclopentane-1-carboxylic acid
Reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH2:8][CH2:7][CH:6]1[C:10]([O:12]C)=[O:11])=[O:4].[OH-].[K+].Cl>CO.O>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH2:8][CH2:7][CH:6]1[C:10]([OH:12])=[O:11])=[O:4]Participants
6
Conditions
- Temperature
- 75 °C
Procedure
Cyclopentane-1,2-dicarboxylic acid dimethyl ester (2.50 g, 13.4 mmol) was dissolved in methanol (2.5 mL) and a solution of potassium hydroxide (85% purity) (920 mg, 13.9 mmol) in methanol (4.0 mL) and water (0.5 mL) in a 25 mL round bottom flask. The reaction mixture was heated at 75° C. for 4 h. The reaction mixture was cooled to 0° C. and acidified to pH 2 with 2M HCl in water. The reaction mixture was diluted with water (100 mL) and extracted with ether. The organic layer was dried over anhydrous magnesium sulfate and concentrated on a rotary evaporator to give cyclopentane-1,2-dicarboxylic acid monomethyl ester as a faint-yellow liquid.
Workup
- temperatureThe reaction mixture was cooled to 0° C.
- extractionextracted with ether
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- concentrationconcentrated on a rotary evaporator
Sources & evidence
- ORD record
- ord-fd3cd0140e3b441aa7aa4d5afd23f234
- Source dataset
- uspto-grants-2008_05
- Patent number
- US07371747B2
Reaction notes
Loading…