Diethyl Malonate → Diethyl (2,2-dimethoxyethyl)malonate

HRID 2291843Notes

Reaction equation

HRID 2291843 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[O-]CC.[Na+].[CH3:16][O:17][CH:18]([O:21][CH3:22])[CH2:19]Br>C(O)C>[CH3:16][O:17][CH:18]([O:21][CH3:22])[CH2:19][CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 816722-Bromo-1,1-dimethoxyethaneHCID 2723922Sodium ethoxide

Product 1

HCID 14215238Diethyl (2,2-dimethoxyethyl)malonateYield 46%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Diethyl malonate (168.18 g, 1.05 mol) was added to a solution of sodium ethoxide (from 23.0 g, 1.00 mol of sodium) in 500 ml of dry ethanol at 50° C. during 45 min. Bromoacetaldehyde dimethylacetal (74.2 g, 1.06 mol) was added at the same temperature during 45 min. and the mixture was refluxed over-night. Ethanol was evaporated in vacuum, and the residue was dissolved in 200 ml of water and extracted with 3×300 ml of ether. The extracts were dried (MgSO4), evaporated, and distilled in vacuum to give 115.0 g (46%) of the title compound. B.p. 97°-101° C. (0.6 mm Hg).

Workup

  1. temperaturethe mixture was refluxed over-night
  2. customEthanol was evaporated in vacuum
  3. dissolutionthe residue was dissolved in 200 ml of water
  4. extractionextracted with 3×300 ml of ether
  5. dry with materialThe extracts were dried (MgSO4)
  6. customevaporated
  7. distillationdistilled in vacuum

Sources & evidence

ORD record
ord-4741fb0ea928427982e5f2d8a5199ba7
Source dataset
uspto-grants-1989_01
Patent number
US04798833

Reaction notes

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