Acetic Acid → 3-Ethoxy-2-methylacrolein dimethylhydrazone

HRID 429512Notes

Reaction equation

HRID 429512 reaction equation
[CH2:1]([O:3][CH:4]=[C:5]([CH3:8])[CH:6]=O)[CH3:2].[CH3:9][N:10]([CH3:12])[NH2:11].C(O)(=O)C>C(OCC)C>[CH3:9][N:10]([CH3:12])[N:11]=[CH:6][C:5]([CH3:8])=[CH:4][O:3][CH2:1][CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 59761,1-DimethylhydrazineHCID 5591983-Ethoxy-2-methyl-2-propenal

Product 1

HCID 541604213-Ethoxy-2-methylacrolein dimethylhydrazone

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 3-ethoxy-2-methyl-2-propenal, (E)- and (Z)- (4.0 g, 35 mmol), 1,1-dimethylhydrazine (2.73 g, 46 mmol) and acetic acid (0.04 g, 0.7 mmol) in diethyl ether is refluxed for one hour, cooled, washed sequentially with water and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give the title product as a yellow oil.

Workup

  1. temperaturecooled
  2. washwashed sequentially with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b6e0a9813e4e48e78850e44f9d941934
Source dataset
uspto-grants-2001_11
Patent number
US06316629B1

Reaction notes

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