Formaldehyde → HCID 131727140, compound

HRID 268745Notes

Reaction equation

HRID 268745 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[CH2:18]=[O:19].[NH2:20]C1C=CC=CC=1>O1CCOCC1.C(OCC)C>[O:19]1[C:18]2[CH:2]=[CH:3][CH:4]=[CH:5][C:8]=2[CH2:11][CH2:16][NH:20]1.[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:11]2[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=2)([CH3:10])[CH3:9])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 6115AnilineHCID 6623Bisphenol A

Product 1

HCID 131727140HCID 131727140, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent2×

Procedure

34.2 g (0.15 mole) of bisphenol-A and 48.6 g (0.6 mole) of aqueous formaldehyde (37%) were added into a 4-neck reactor equipped with a stirrer, temperature controller, and condenser, and then 100 ml of 1,4-dioxane was added as a solvent. The mixture was stirred at room temperature, and to the resulting solution 27.9 g aniline in 30 ml 1,4-dioxane was dripped at a rate of one drop per second while stirring. Upon completion of the dripping the solution was heated and reacted under refluxing for 10 hours. The reaction mixture was dried in a rotary evaporator under vacuum to obtain a yellowish solid. The yellowish solid was dissolved in ethyl ether and washed with 3N aqueous NaOH three times, followed by 1 N aqueous HCl solution several times and pure water several times, before removing the solvent in vacuo. The dried solid was ground to obtain bisphenol-A dihydrobenzoxazine powder, which is yellowish white. m.p. 110° C. EA: Calcd.: C: 80.50%; H: 6.49%; N: 6.00%. Found: C: 80.00%; H: 6.56%; N: 6.08%.

Workup

  1. customequipped with a stirrer
  2. stirringwhile stirring
  3. temperatureUpon completion of the dripping the solution was heated
  4. customreacted
  5. temperatureunder refluxing for 10 hours
  6. customThe reaction mixture was dried in a rotary evaporator under vacuum
  7. customto obtain a yellowish solid
  8. washwashed with 3N aqueous NaOH three times
  9. custombefore removing the solvent in vacuo

Sources & evidence

ORD record
ord-ba69055a2e7f46e09953f04eb011b0f7
Source dataset
uspto-grants-2008_11
Patent number
US07446160B2

Reaction notes

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