Formaldehyde → Benzoxazines

HRID 1261548Notes

Reaction equation

HRID 1261548 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:8]=[O:9].O[C:11]1C=CC(C2C=CC(O)=CC=2)=CC=1>O1CCOCC1>[O:9]1[C:8]2[CH:11]=[CH:3][CH:4]=[CH:5][C:6]=2[CH:7]=[CH:2][NH:1]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 6115AnilineHCID 71124,4'-Dihydroxybiphenyl

Product 1

HCID 17845026BenzoxazinesYield 292.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a flask of 0.5 L in volume, 71.7 g (0.77 mol) of aniline and 150 mL of dioxane were placed and the mixture was stirred to dissolve. Then, 37.3 g of a formaldehyde solution (a 36 to 38% aqueous solution) was added dropwise to be reacted at room temperature for 2 hours. Thereafter, 71.5 g (0.38 mol) of 4,4′-dihydroxybiphenyl was added to be reacted with stirring at 100 to 110° C. for 6 hours. After completion of the reaction, a precipitate was filtrated and dried in a vacuum drier at 95° C. for 8 hours to obtain 148 g of the compound (E-1) having at least two benzoxazine rings and represented by the formula (15) below.

Workup

  1. dissolutionto dissolve
  2. customto be reacted at room temperature for 2 hours
  3. customto be reacted
  4. stirringwith stirring at 100 to 110° C. for 6 hours
  5. customAfter completion of the reaction
  6. filtrationa precipitate was filtrated
  7. customdried in a vacuum drier at 95° C. for 8 hours

Sources & evidence

ORD record
ord-25ed945f6951465ab13793d3113fd1d9
Source dataset
uspto-grants-2013_06
Patent number
US08470918B2

Reaction notes

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