Formaldehyde → HCID 54059009, compound

HRID 429510Notes

Reaction equation

HRID 429510 reaction equation
S(=O)(=O)(O)O.[CH3:6][N:7]([CH3:12])[CH:8]=[CH:9][CH:10]=[O:11].[CH2:13]=[O:14].[CH3:15]O>>[CH3:6][N:7]([CH3:12])[CH:8]=[C:9]([CH2:13][O:14][CH3:15])[CH:10]=[O:11]

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 887MethanolHCID 1118Sulfuric AcidHCID 791253-(Dimethylamino)-2-propenal

Product 1

HCID 54059009HCID 54059009, compoundYield 87%

Procedure

Concentrated sulfuric acid (1 mL) is slowly added to a solution of 3-(dimethylamino)-2-propenal (200 g, 2.01 mol) and paraformaldehyde (90 g, 3 mol) in methanol (1 L). The resultant solution is refluxed overnight, concentrated in vacuo to a volume of 200 mL, diluted with toluene and distilled until the vapor temperature is 105° C. The solution is then concentrated in vacuo to give the title product as an orange oil (251.4 g, 87% yield).

Workup

  1. concentrationconcentrated in vacuo to a volume of 200 mL
  2. additiondiluted with toluene
  3. distillationdistilled until the vapor temperature
  4. customis 105° C
  5. concentrationThe solution is then concentrated in vacuo

Sources & evidence

ORD record
ord-f63eaa76e2d3497e980b50660a7a53af
Source dataset
uspto-grants-2001_11
Patent number
US06316629B1

Reaction notes

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