Diethylene Glycol Monoethyl Ether → HCID 13137098, compound

HRID 1702221Notes

Reaction equation

HRID 1702221 reaction equation
[CH:1]([CH:3]1[CH2:5][C:4]1([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH2:2].[CH2:16]([O:18][CH2:19][CH2:20][O:21]CCO)[CH3:17]>[O-]CC.[Na+].C(O)C>[CH:1]([CH:3]1[CH2:5][C:4]1([C:11]([O:13][CH2:14][CH2:15][O:21][CH2:20][CH2:19][O:18][CH2:16][CH3:17])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH2:2]

Participants

5

Reactant 2

HCID 8146Diethylene Glycol Monoethyl EtherHCID 111025Diethyl 2-vinylcyclopropane-1,1-dicarboxylate2×

Product 1

HCID 13137098HCID 13137098, compound

Reagents, catalysts & solvents 2

HCID 2723922Sodium ethoxideCatalystHCID 702EthanolSolvent

Procedure

Employing a procedure similar to that of Example IV diethyl 2-vinylcyclopropane-1,1-dicarboxylate was reacted with a polyalkoxylated alcohol in the presence of sodium ethoxide catalyst. For the process 33.77 g (0.159 mol) diethyl 2-vinylcyclopropane-1,1-dicarboxylate and 7.12 g (0.053 mol) 2-(2-ethoxyethoxy)ethanol were heated at reflux until the theoretical amount of ethanol was recovered. After removal of unreacted diethyl 2-vinylcyclopropane-1,1-dicarboxylate (19.63 g), 8.4 g crude ethyl 2-(2-ethoxyethoxy)ethyl 2-vinylcyclopropane-1,1-dicarboxylate was obtained. Redistillation of the crude product provided 4.9 g high purity 2-(2-ethoxyethoxy)ethyl 2-vinylcyclopropane-1,1-dicarboxylate. B.p. 110°-112° C. at 0.01 mm Hg; nD24.5 1.4608. Infrared and nuclear magnetic resonance spectra were consistent with the desired structure.

Workup

  1. customwas recovered
  2. customAfter removal of unreacted diethyl 2-vinylcyclopropane-1,1-dicarboxylate (19.63 g)

Sources & evidence

ORD record
ord-092d3a988f0349eab548ed5cc6c0ce14
Source dataset
uspto-grants-1983_04
Patent number
US04380656

Reaction notes

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