Diethyl Malonate → HCID 2237931, compound
Reaction equation
[CH2:1]([O:3][C:4](=[O:11])[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].CC[O-].[Na+].[Na].[CH3:17][C:18]1[CH:29]=[CH:28][C:21]([O:22][CH2:23][CH2:24][CH2:25][CH2:26]Br)=[CH:20][CH:19]=1>C(O)C>[CH2:1]([O:3][C:4](=[O:11])[CH:5]([CH2:26][CH2:25][CH2:24][CH2:23][O:22][C:21]1[CH:20]=[CH:19][C:18]([CH3:17])=[CH:29][CH:28]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
176.2 g of malonic acid diethyl ester are added dropwise at 50° C. to a sodium ethylate solution freshly prepared from 23 g of sodium and 500 ml of ethanol. The mixture is kept at this temperature for 2 hours, and 243.2 g of 4-(4-methylphenoxy)butyl bromide are then added dropwise. When the addition is complete, the obtained mixture is stirred at 60° C. for 3 hours, and substantially concentrated; 1 l of ice-water is then added and the mixture is extracted 3 times with a total of 1 liter of methylene chloride. The combined organic phases are dried over sodium sulfate, and the solvent and the excess malonic acid diethyl ester is distilled off in vacuo. 303.9 g of 4-(4-methylphenoxy)butylmalonic acid diethyl ester are obtained as pale yellow, oily residue.
Workup
- additionWhen the addition
- concentrationsubstantially concentrated
- addition1 l of ice-water is then added
- extractionthe mixture is extracted 3 times with a total of 1 liter of methylene chloride
- dry with materialThe combined organic phases are dried over sodium sulfate
- distillationthe solvent and the excess malonic acid diethyl ester is distilled off in vacuo
Sources & evidence
- ORD record
- ord-6e9d17dd544b4fcdb52f57daa4ccd1df
- Source dataset
- uspto-grants-1982_06
- Patent number
- US04337267
Reaction notes
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