Formaldehyde → Benzoxazines

HRID 351945Notes

Reaction equation

HRID 351945 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)O.[CH2:9]([NH2:12])[CH:10]=C.C=O>C1(C)C=CC=CC=1>[O:6]1[C:5]2[CH:4]=[CH:3][CH:1]=[CH:8][C:7]=2[CH:10]=[CH:9][NH:12]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 785HydroquinoneHCID 7853Allylamine

Product 1

HCID 17845026Benzoxazines

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Hydroquinone (8.23 g, 75 mmol), allylamine (8.57 g, 150 mmol) and toluene (100 mL) were placed in a 250 mL flask. Paraformaldehyde (9.0 grams, equivalent to 300 mmole formaldehyde) was added along with a magnetic stir bar. The flask was equipped as described in Example 1 and brought to reflux. The full theoretical amount of water was collected within forty-five minutes of reflux. The toluene solution was washed with six 25 ml portions of 5% aqueous sodium hydroxide, and three 30 ml aliquots of water. The toluene solution was then dried over anhydrous magnesium sulfate and then passed over 26 grams of activated, neutral alumina. The toluene was removed to yield 11.0 grams (54% of theory) of a red, semi-solid material.

Workup

  1. customThe flask was equipped
  2. temperatureto reflux
  3. customThe full theoretical amount of water was collected within forty-five minutes
  4. temperatureof reflux
  5. washThe toluene solution was washed with six 25 ml portions of 5% aqueous sodium hydroxide, and three 30 ml aliquots of water
  6. dry with materialThe toluene solution was then dried over anhydrous magnesium sulfate
  7. customThe toluene was removed
  8. customto yield 11.0 grams (54% of theory) of a red, semi-solid material

Sources & evidence

ORD record
ord-fda65a80bb584d429f0b09fa38d27adf
Source dataset
uspto-grants-2004_06
Patent number
US06743852B2

Reaction notes

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