Guaiacol → HCID 12268981, compound

HRID 258806Notes

Reaction equation

HRID 258806 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][CH:19]=[CH:18][C:14]=1[CH2:15][CH2:16][NH2:17].[O:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1>>[Cl:12][C:13]1[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=1[CH2:15][CH2:16][N:17]1[CH2:7][C:8]2[CH:3]=[CH:4][CH:5]=[C:27]([O:22][CH3:23])[C:26]=2[O:25][CH2:24]1

Participants

5

Reactant 4

HCID 460GuaiacolHCID 712FormaldehydeHCID 312751,4-DioxaneHCID 831172-(2-Chlorophenyl)ethylamine

Product 1

HCID 12268981HCID 12268981, compound

Procedure

To 120 ml. of dioxane are added 5 g. of ortho-methoxyphenol, 9 ml. of 37% formalin and 7.56 g. of ortho-chlorophenethylamine. 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 cooled to be solidified. Recrystallization from methanol yields 3-(2-chlorophenethyl)-8-methoxy-3,4-dihydro-2H-1,3-benzoxazine as colorless needles melting at 79°-81° C. Yield: 6 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. temperatureThe resultant oil is cooled
  7. customRecrystallization from methanol

Sources & evidence

ORD record
ord-76aba193c8f0492fbfd117311b121097
Source dataset
uspto-grants-1977_07
Patent number
US04035363

Reaction notes

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