Carbon Dioxide → HCID 54419238, compound
Reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH:5]([CH2:9][CH2:10][CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[C:6](O)=O)[CH3:2].C=O.N1CCCCC1.C(=O)=O>O.N1C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:18])[C:5](=[CH2:6])[CH2:9][CH2:10][CH2:11][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1)[CH3:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
51 g of (3-cyclohexylpropyl)-malonic acid ethyl ester, 6.4 g of paraformaldehyde, 50 ml of pyridine and 2.1 g of piperidine are warmed to 60° C. When the evolution of carbon dioxide is complete (approx. 1 hour), the mixture is stirred for a further hour at 60° C. and is poured into 800 ml of water and the mixture is extracted with 4 times 200 ml of petroleum ether. The combined organic phases are washed with 200 ml of water, 200 ml of 2 N hydrochloric acid, 200 ml of water and 200 ml of saturated sodium bicarbonate solution and are dried over sodium sulphate and concentrated. The residue is purified by chromatography on a silica gel column. (Migrating agent 80:20 petroleum ether/ethyl acetate). This gives 36.7 g of 5-cyclohexyl-2-methylenevaleric acid ethyl ester in the form of a nearly colourless oil.
Workup
- custom(approx. 1 hour)
- extractionthe mixture is extracted with 4 times 200 ml of petroleum ether
- washThe combined organic phases are washed with 200 ml of water, 200 ml of 2 N hydrochloric acid, 200 ml of water and 200 ml of saturated sodium bicarbonate solution
- dry with materialare dried over sodium sulphate
- concentrationconcentrated
- customThe residue is purified by chromatography on a silica gel column
Sources & evidence
- ORD record
- ord-e31e88bcd8bb4289ac2c8eb77803514e
- Source dataset
- uspto-grants-1984_02
- Patent number
- US04430339
Reaction notes
Loading…