Guaiacol → HCID 50177, compound

HRID 258804Notes

Reaction equation

HRID 258804 reaction equation
[CH2:1]=O.[CH2:3]([NH2:11])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[OH:20]>O1CCOCC1>[CH3:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:1][NH:11][CH2:3][CH2:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:15]=1[OH:20]

Participants

5

Reactant 3

HCID 460GuaiacolHCID 712FormaldehydeHCID 1001Phenethylamine

Product 1

HCID 50177HCID 50177, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
100 °C

Procedure

To 10 ml. of dioxane are added 1.5 ml. of 37 % formalin and 2.42 g. of phenethylamine, followed by the addition of 3.2 g. of ortho-methoxyphenol dissolved in 3 ml. of dioxane. The mixture is heated at 100° C for 4 hours and distilled under reduced pressure to remove the solvent. The residue is purified by column chromatography on silica gel with a mixture of acetone and benzene (1:4) to obtain 2-methoxy-6-phenethylaminomethylphenol as an oil. Yield: 0.7 g.

Workup

  1. distillationdistilled under reduced pressure
  2. customto remove the solvent
  3. customThe residue is purified by column chromatography on silica gel with a mixture of acetone and benzene (1:4)

Sources & evidence

ORD record
ord-95daad149fa6438499448a44f148ac8b
Source dataset
uspto-grants-1977_07
Patent number
US04035363

Reaction notes

Loading…