Guaiacol → 4-Methoxy-1-methyl-2-phenoxybenzene

反応式

O[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9].Br[C:11]1[CH:16]=[CH:15]C=[CH:13][CH:12]=1.[C:17]([O-:20])([O-])=O.[K+].[K+].N1C=CC=C[CH:24]=1>>[CH3:24][C:6]1[CH:5]=[CH:4][C:3]([O:8][CH3:9])=[CH:2][C:7]=1[O:20][C:17]1[CH:15]=[CH:16][CH:11]=[CH:12][CH:13]=1

参加物

反応物 4

HCID 460Guaiacol

HCID 1049Pyridine

HCID 7961Bromobenzene2 回

HCID 11430Potassium Carbonate

生成物 1

HCID 537769894-Methoxy-1-methyl-2-phenoxybenzene収率 51.7%

反応条件

温度: 70 °C

実験手順

Into 50 mL pyridine, was added 4.14 g (30 mmoles) of the hydroxyanisole prepared above, 3.48 mL (33 mmoles) of bromobenzene, and 4.8 g (60 mmoles) of K2CO3. Under argon, the mixture was heated to 70° C., and 4.8 g (60 mmoles) of powdered CuO was added. The mixture was then heated for 16 hours at reflux with vigorous stirring. Additional CuO (4.8 g,60 mmoles) and bromobenzene (3.5 mL, 60 mmoles) were added, and the reaction mixture was heated 16 hours at reflux. After cooling and filtering, the reaction mixture was evaporated under vacuum. The residue was extracted between EtOAC and cold dilute HCl three times. The organic layer was dried over Na2SO4, filtered and evaporated under vacuum. The product was purified via silica gel flash chromatography (0 to 30% EtOAc in hexane), giving 3.32 g (51.7%) 4-methyl-3-phenoxyanisole as an oil.