Formaldehyde → Benzoxazines

HRID 351944Notes

Reaction equation

HRID 351944 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)O.C(OC[CH2:13][CH2:14][NH2:15])=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:13]=[CH:14][NH:15]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 785HydroquinoneHCID 43863963-(Vinyloxy)propan-1-amine

Product 1

HCID 17845026Benzoxazines

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Hydroquinone (8.23 grams, 75 mmole), 3-amino-1-propanol vinyl ether (15.1 grams, 150 mmole), and toluene (100 mL) were placed in a 250 mL round bottom flask. Paraformaldehyde (9.0 grams, equivalent to 300 mmole of formaldehyde) was then added to the flask. The flask was then equipped with a magnetic stir bar, a Dean-Stark trap, and condenser. The mixture was stirred and heated to reflux under an argon blanket. A total of 5.2 milliliters (96% of theory) of water was collected in the trap after two hours reflux. The reaction mixture had turned black by this point. The toluene reaction solution was washed with two 50 mL aliquots of 5% aqueous sodium hydroxide, followed by one 50 mL aliquot of water. The toluene solution was passed over a bed of neutral alumina and then evaporated to yield 3.8 grams (14% of theory) of a viscous, light brown liquid.

Workup

  1. customThe flask was then equipped with a magnetic stir bar
  2. temperatureheated
  3. temperatureto reflux under an argon blanket
  4. customA total of 5.2 milliliters (96% of theory) of water was collected in the trap after two hours
  5. temperaturereflux
  6. customThe toluene reaction solution
  7. washwas washed with two 50 mL aliquots of 5% aqueous sodium hydroxide
  8. customevaporated
  9. customto yield 3.8 grams (14% of theory) of a viscous, light brown liquid

Sources & evidence

ORD record
ord-64b8cdc59fa040aab96311f3675dbf33
Source dataset
uspto-grants-2004_06
Patent number
US06743852B2

Reaction notes

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