3,5-Dimethoxyphenol → 1-(3-Chloropropoxy)-3,5-dimethoxybenzene

반응식

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:11])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[Cl:12][CH:13](Br)[CH2:14][CH3:15].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:12][CH2:13][CH2:14][CH2:15][O:11][C:5]1[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1

참가 물질

실험 절차

A mixture of 3,5-dimethoxyphenol 100.0 g (0.6486 mole), chlorobromopropane 148.0 g (0.96 mole) and potassium carbonate 89.6 g (0.96 mole) was heated overnight at gentle reflux in 600 ml of acetone. The reaction mixture was cooled at room temperature, filtered, and stripped to dryness via a rotary evaporator. The resulting oil was dissolved in chloroform and the solution extracted with 5% aqueous sodium hydroxide; removal of chloroform gave a dark brown oil. A 5-g sample of the oil was pumped in vacuo overnight at 80° C. This produced 3.23 g (53.2% yield based on the aliquot taken) of dark brown oil. H1 (CDCl3): δ 2-2.14 (quintuplet, center methylene protons, 2H), 3.6-4.2 (m, aliphatic protons, 4H), 3.8 (s, OCH3, 6H), 6.1 (s,aromatic protons, 3H).