Formaldehyde → HCID 69102806, compound

HRID 268746Notes

Reaction equation

HRID 268746 reaction equation
[C:1]1([OH:14])[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.[CH2:15]=[O:16].[NH2:17]C1C=CC=CC=1>O1CCOCC1.C(OCC)C>[O:16]1[C:15]2[CH:1]=[CH:2][CH:3]=[CH:4][C:7]=2[CH2:8][CH2:9][NH:17]1.[C:10]1([OH:13])[CH:9]=[CH:8][C:7]([C:4]2[CH:5]=[CH:6][C:1]([OH:14])=[CH:2][CH:3]=2)=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 6115AnilineHCID 71124,4'-Dihydroxybiphenyl

Product 1

HCID 69102806HCID 69102806, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent2×

Procedure

27.9 g of 4,4′-biphenol and 48.6 g of aqueous formaldehyde (37%) were added into a 4-neck reactor equipped with a stirrer, temperature controller, and condenser, and then 80 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 pale orange solid. The pale orange solid was dissolved in ethyl ether and washed with 3N NaOH aqueous three times, followed by 1 N aqueous HCl solution several times and pure water several times, before removing the solvent in vacuo to obtain pale orange 4,4′-biphenol dihydrobenzoxazine solid. m.p. 170° C. EA: Calcd.: C: 80.00%; H: 5.71%; N: 6.66%. Found: C: 80.30%; H: 5.73%; N: 6.56%.

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 pale orange solid
  8. washwashed with 3N NaOH aqueous three times
  9. custombefore removing the solvent in vacuo

Sources & evidence

ORD record
ord-6b1caf9004f046e7b2a03089ab14b727
Source dataset
uspto-grants-2008_11
Patent number
US07446160B2

Reaction notes

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