Guaiacol → 2H-1,3-Benzoxazine, 3,4-dihydro-8-methoxy-3-(2-(4-methoxyphenyl)ethyl)-

HRID 258809Notes

Reaction equation

HRID 258809 reaction equation
CO[C:3]1[CH:8]=[CH:7]C=[CH:5][C:4]=1O.C=O.[CH3:12][O:13][C:14]1[CH:22]=[CH:21][C:17]([CH2:18][CH2:19][NH2:20])=[CH:16][CH:15]=1.[O:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>>[CH3:27][O:26][C:25]1[C:24]2[O:23][CH2:28][N:20]([CH2:19][CH2:18][C:17]3[CH:21]=[CH:22][C:14]([O:13][CH3:12])=[CH:15][CH:16]=3)[CH2:7][C:8]=2[CH:3]=[CH:4][CH:5]=1

Participants

5

Reactant 4

HCID 460GuaiacolHCID 712FormaldehydeHCID 4657O-MethyltyramineHCID 312751,4-Dioxane

Product 1

HCID 30432782H-1,3-Benzoxazine, 3,4-dihydro-8-methoxy-3-(2-(4-methoxyphenyl)ethyl)-

Procedure

To 20 ml. of dioxane are added 5 g. of ortho-methoxyphenol, 9 ml. of 37 % formalin and 6.7 g. of para-methoxyphenethylamine. The mixture is heated on reflux for 4 hours and concentrated to dryness under reduced pressure. The residue is purified by column chromatography on silica gel with a mixture of acetone and benzene (1:4). The resultant oily substance is left standing at cool place for one month to be solidified. Recrystallization from petroleum ether yields 8-methoxy-3-(4-methoxyphenethyl)-3,4-dihydro-2H-1,3-benzoxazine as melting at 69°-70° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureon reflux for 4 hours
  3. concentrationconcentrated to dryness under reduced pressure
  4. customThe residue is purified by column chromatography on silica gel with a mixture of acetone and benzene (1:4)
  5. waitThe resultant oily substance is left
  6. temperatureat cool place for one month
  7. customRecrystallization from petroleum ether

Sources & evidence

ORD record
ord-3642b93c08ce4b30be0c3da7cb6ab868
Source dataset
uspto-grants-1977_07
Patent number
US04035363

Reaction notes

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