Formaldehyde → 1,3-Dioxan-5-yl 3-pyridyl ketone

HRID 354718Notes

Reaction equation

HRID 354718 reaction equation
[C:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].[CH2:10]=[O:11].B(F)(F)F.C[CH2:17][O:18][CH2:19]C>C(O)(=O)C>[N:6]1[CH:7]=[CH:8][CH:9]=[C:4]([C:1]([CH:2]2[CH2:10][O:11][CH2:19][O:18][CH2:17]2)=[O:3])[CH:5]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8000Boron trifluoride etherateHCID 95893-Acetylpyridine

Product 1

HCID 119709961,3-Dioxan-5-yl 3-pyridyl ketone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A 48.4 g. portion of 3-acetylpyridine was combined with 60 g. of paraformaldehyde and 200 ml. of glacial acetic acid, and to the mixture was added, dropwise with stirring, 86 g. of boron trifluoride etherate. The mixture was then heated, and was stirred under reflux for 4 hours. The reaction was cooled and the volatile materials were evaporated under vacuum to obtain 60 g. of an oily yellow solid, which was crystallized by the addition of water. The solids were separated by filtration, washed with water and dried to obtain 25 g. of the desired product, m.p. 91°-100°.

Workup

  1. temperatureThe mixture was then heated
  2. stirringwas stirred
  3. temperatureunder reflux for 4 hours
  4. temperatureThe reaction was cooled
  5. customthe volatile materials were evaporated under vacuum
  6. customto obtain 60 g
  7. customof an oily yellow solid, which was crystallized by the addition of water
  8. customThe solids were separated by filtration
  9. washwashed with water
  10. customdried
  11. customto obtain 25 g

Sources & evidence

ORD record
ord-5e17a6783e384cc4bcdd068d1263980e
Source dataset
uspto-grants-1983_03
Patent number
US04376860

Reaction notes

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