Formaldehyde → Benzoxazines

HRID 2174588Notes

Reaction equation

HRID 2174588 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C)C=CC=CC=1.[NH2:15][C:16]1C=CC=C[CH:17]=1.C=O>C(O)C>[O:7]1[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=2[CH:17]=[CH:16][NH:15]1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 996PhenolHCID 1140TolueneHCID 6115Aniline

Product 1

HCID 17845026BenzoxazinesYield 78.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

At room temperature, phenol was dissolved in anhydrous ethanol; the pH was adjusted to 8-10; toluene, aniline and paraformaldehyde were added according to the molar ratio of phenolic hydroxyl group:amine group:aldehyde group of 1:1.2:2.5. After being homogeneously stirred, the mixture was heated and refluxed, reacted for 4 h to vacuum distill off ethanol, water, toluene, and placed in a cooling unit. Butanone was added to obtain a yellowish, translucent viscous body. The viscous body was washed, purified and dried to obtain a benzoxazine intermediate having the following structural formula, wherein the yield is 78.8%.

Workup

  1. temperaturethe mixture was heated
  2. temperaturerefluxed
  3. customreacted for 4 h to vacuum
  4. distillationdistill off ethanol, water, toluene
  5. additionButanone was added
  6. customto obtain a yellowish, translucent viscous body
  7. washThe viscous body was washed
  8. custompurified
  9. customdried

Sources & evidence

ORD record
ord-7404a85e19ca44ccadd393805e678408
Source dataset
uspto-grants-2015_06
Patent number
US09062011B2

Reaction notes

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