Formaldehyde → 2H-1,3-Benzoxazine, 3,4-dihydro-8-methoxy-3-(2-phenylethyl)-

HRID 258805Notes

Reaction equation

HRID 258805 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][NH:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:4]=1[OH:19].[CH2:20]=O>O1CCOCC1>[CH3:1][O:2][C:3]1[C:4]2[O:19][CH2:20][N:10]([CH2:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:9][C:5]=2[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 50177HCID 50177, compound

Product 1

HCID 30432752H-1,3-Benzoxazine, 3,4-dihydro-8-methoxy-3-(2-phenylethyl)-

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To 5 ml. of dioxane are added 0.6 g. of 2-methoxy-6-phenethylaminomethylphenol prepared as above and 1 ml. of 37 % formalin. The mixture is heated on reflux for 3 hours and distilled to remove the solvent. The residue is purified by column chromatography on silica gel with a mixture of acetone and benzene (1:4). The resultant oil is left standing at cool place for 2-3 days to be solidified. Recrystallization from normal hexane yields 8-methoxy-3-phenethyl-3,4-dihydro-2H-1,3-benzoxazine as colorless needles melting at 63°-66° C. Yield: 0.4 g.

Workup

  1. temperatureThe mixture is heated
  2. temperatureon reflux for 3 hours
  3. distillationdistilled
  4. customto remove the solvent
  5. customThe residue is purified by column chromatography on silica gel with a mixture of acetone and benzene (1:4)
  6. waitThe resultant oil is left
  7. temperatureat cool place for 2-3 days
  8. customRecrystallization from normal hexane

Sources & evidence

ORD record
ord-030ee76780794a679f69f9862782f288
Source dataset
uspto-grants-1977_07
Patent number
US04035363

Reaction notes

Loading…