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

반응식

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

참가 물질

반응물 4

HCID 460Guaiacol

HCID 1049Pyridine

HCID 7961Bromobenzene2회

HCID 11430Potassium Carbonate

생성물 1

HCID 537769894-Methoxy-1-methyl-2-phenoxybenzene수율 51.7%

반응 조건

온도: 70 °C

실험 절차

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.