Benzene → HCID 21424658, compound

HRID 258808Notes

Reaction equation

HRID 258808 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1O.[CH2:10]=[O:11].[CH3:12][C:13]1[CH:21]=[CH:20][C:16]([CH2:17][CH2:18][NH2:19])=[CH:15][CH:14]=1.[CH:22]1C=CC=CC=1>>[CH3:10][O:11][C:8]1[C:3]2[O:2][CH2:1][N:19]([CH2:18][CH2:17][C:16]3[CH:20]=[CH:21][C:13]([CH3:12])=[CH:14][CH:15]=3)[CH2:22][C:4]=2[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 241BenzeneHCID 460GuaiacolHCID 712FormaldehydeHCID 76751p-Methylphenethylamine

Product 1

HCID 21424658HCID 21424658, compound

Procedure

To 20 ml. of benzene are added 5g. of ortho-methoxyphenol, 9ml. of 37 % formalin and 6.5 g. of para-methylphenethylamine. The mixture is heated on reflux for 10 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 oil is left standing at cool place for a week to be solidified. Recrystallization from normal hexane yields 8-methoxy-3-(4-methylphenethyl)-3,4-dihydro-2H-1,3-benzoxazine as colorless needles melting at 58°-63° C. Yield: 1.2 g.

Workup

  1. temperatureThe mixture is heated
  2. temperatureon reflux for 10 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 oil is left
  6. temperatureat cool place for a week
  7. customRecrystallization from normal hexane

Sources & evidence

ORD record
ord-a243c5dde464430ba1504381225d8c0a
Source dataset
uspto-grants-1977_07
Patent number
US04035363

Reaction notes

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