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

HRID 258807Notes

Reaction equation

HRID 258807 reaction equation
CO[C:3]1[CH:8]=[CH:7]C=[CH:5][C:4]=1O.C=O.[Cl:12][C:13]1[CH:21]=[CH:20][C:16]([CH2:17][CH2:18][NH2:19])=[CH:15][CH:14]=1.[O:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1>>[Cl:12][C:13]1[CH:21]=[CH:20][C:16]([CH2:17][CH2:18][N:19]2[CH2:7][C:8]3[CH:3]=[CH:4][CH:5]=[C:27]([O:22][CH3:23])[C:26]=3[O:25][CH2:24]2)=[CH:15][CH:14]=1

Participants

5

Reactant 4

HCID 460GuaiacolHCID 712FormaldehydeHCID 312751,4-DioxaneHCID 674302-(4-Chlorophenyl)ethylamine

Product 1

HCID 30432772H-1,3-Benzoxazine, 3,4-dihydro-3-(2-(4-chlorophenyl)ethyl)-8-methoxy-

Procedure

To 20 ml. of dioxane are dissolved 5 g. of orthomethoxyphenol, 5 g. of para-formaldehyde and 12.6 g. of para-chlorophenethylamine. The solution is heated on reflux for 9.5 hours and distilled to remove the solvent. The residue is purified by column chromatography on silica gel with a mixture of acetone and benezene (1:4). Recrystallization of the resultant crude crystals from methanol yields 3-(4-chlorophenethyl)-8-methoxy-3,4-dihydro-2H-1,3-benzoxazine as colorless needles melting at 87-88° C. Yield: 4 g.

Workup

  1. temperatureThe solution is heated
  2. temperatureon reflux for 9.5 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 benezene (1:4)
  6. customRecrystallization of the resultant crude crystals from methanol

Sources & evidence

ORD record
ord-b18034c443374f7194b47c4b9e248bc2
Source dataset
uspto-grants-1977_07
Patent number
US04035363

Reaction notes

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