Formaldehyde → 2-(Morpholinomethyl)acrylic acid

HRID 1069009Notes

Reaction equation

HRID 1069009 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH2:7]=O.[C:9](O)(=O)[CH2:10][C:11]([OH:13])=[O:12]>O1CCOCC1>[N:1]1([CH2:7][C:10](=[CH2:9])[C:11]([OH:13])=[O:12])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 867Malonic AcidHCID 8083Morpholine

Product 1

HCID 103972322-(Morpholinomethyl)acrylic acidYield 32%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In a manner described by Krawczyk [Henryk Krawczyk, Synthetic Communications, 25 641-650, (1995)] an 8.8 mL (8.8 g; 0.1 mole) portion of morpholine was added to 6.6 g (0.22 eq) of paraformaldehyde and 10.4 g (0.1 mole) of malonic acid in 100 mL of dioxane. After heating in an oil bath at 70 deg for 1 {fraction (1/12)} hours, the solvents were removed in vacuo. The residue was dissolved in acetone, some insoluble material being filtered. The filtrate was taken to an oil in vacuo. This oil was chromatographed on silica gel. Elution of the product with 1:19 methanol methylene chloride gave 5.51 g (32%) of the product, which melted at 121-125° C.

Workup

  1. customthe solvents were removed in vacuo
  2. dissolutionThe residue was dissolved in acetone
  3. filtrationsome insoluble material being filtered
  4. customThis oil was chromatographed on silica gel
  5. washElution of the product with 1:19 methanol methylene chloride

Sources & evidence

ORD record
ord-5701ceeb14254d90ab4ec3bcff23941f
Source dataset
uspto-grants-2001_06
Patent number
US06251912B1

Reaction notes

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