Formaldehyde → HCID 12440978, compound

HRID 1282985Notes

Reaction equation

HRID 1282985 reaction equation
[CH3:1][C:2]1([CH3:11])[CH2:7][CH:6]([OH:8])[CH2:5][C:4]([CH3:10])([CH3:9])[NH:3]1.[CH2:12]=[O:13]>N1C=CC=CC=1>[OH:13][CH2:12][N:3]1[C:4]([CH3:10])([CH3:9])[CH2:5][CH:6]([OH:8])[CH2:7][C:2]1([CH3:11])[CH3:1]

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 754714-Hydroxy-2,2,6,6-tetramethylpiperidine

Product 1

HCID 12440978HCID 12440978, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a 1-liter stainless steel container are placed 79 grams of 2, 2, 6, 6-tetramethyl-4-hydroxypiperidine, 132 grams of paraformaldehyde and 300 milliliters of pyridine. The flask is evacuated, filled with nitrogen and this process repeated 3 times. The flask is then sealed and heated at 135° to 140°C. for 30 minutes with rocking. The flask is then cooled quickly to room temperature, the contents removed and the mixture filtered. The pyridine is removed from the filtrate on a rotary evaporator. The remaining viscous oil is dissolved in ether, treated with activated charcoal, brought to a boil and filtered. The ether is removed from the filtrate on a rotary evaporator to yield 1-hydroxymethyl-2, 2, 6, 6 -tetramethyl-4-hydroxypiperidine as a viscous oil.

Workup

  1. customThe flask is evacuated
  2. additionfilled with nitrogen
  3. customThe flask is then sealed
  4. temperatureheated at 135° to 140°C. for 30 minutes with rocking
  5. customthe contents removed
  6. filtrationthe mixture filtered
  7. customThe pyridine is removed from the filtrate on a rotary evaporator
  8. dissolutionThe remaining viscous oil is dissolved in ether
  9. additiontreated with activated charcoal
  10. filtrationfiltered
  11. customThe ether is removed from the filtrate on a rotary evaporator

Sources & evidence

ORD record
ord-a2c3bb29d08a47ac8bc3fc93a7fc9a3b
Source dataset
uspto-grants-1976_08
Patent number
US03974127

Reaction notes

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