Formaldehyde → HCID 86718774, compound

HRID 929595Notes

Reaction equation

HRID 929595 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:14]=[O:15].[C:16]([NH2:20])([CH3:19])([CH3:18])[CH3:17].[CH:21](O)(C)C>C(OCC)(=O)C>[C:16]([N:20]1[CH2:21][C:5]2[CH:4]=[CH:3][CH:2]=[C:1]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:6]=2[O:15][CH2:14]1)([CH3:19])([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 3776IsopropanolHCID 6385Tert-ButylamineHCID 7017(1,1'-Biphenyl)-2-ol

Product 1

HCID 86718774HCID 86718774, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2-phenylphenol (17.0 g, 0.1 mol) and paraformaldehyde (15.0 g, 0.5 mol) in isopropanol (100 mL) was added tert-butylamine (36.5 g, 0.5 mol) dropwise. The resulting reaction mixture was refluxed under nitrogen overnight. The cooled reaction mixture was then concentrated under reduced pressure to give a yellow oil. The yellow oil was dissolved in ethyl acetate to form a solution which was washed with water, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford 3-(tert-butyl)-8-phenyl-3,4-dihydro-2H-benzo[e][1,3]oxazine (30 g) as yellow oil.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas refluxed under nitrogen overnight
  3. customThe cooled reaction mixture
  4. concentrationwas then concentrated under reduced pressure
  5. customto give a yellow oil
  6. customto form a solution which
  7. washwas washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2a77b3548a014ec58325af13ef510187
Source dataset
uspto-grants-2016_03
Patent number
US09296696B2

Reaction notes

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