Reaction Steps
2,6-Diallylphenol (5.2 g, 0.03 mol) was diluted with 95% ethanol (50 ml). Sodium hydroxide (1.4 gm, 0.03 mol) was added to the phenol solution followed by 2-chloroethylether (3.8 gm, 0.035 mol). The reaction mixture was refluxed for 48 hrs, cooled, diluted with water, extracted with hexane and dried over MgSO4. Filtration of the MgSO4 and evaporation of the hexane gave 5.1 g of 2,6-diallylphenyl ethoxyethyl ether. MS m/z 246 (M+ calcd for C16H22O2=246). H NMR (300 MHz, CDCl3) d 1.30 (3, t, CH3), 3.40–3.55 (4, m, CH2 allyl), 3.65–3.75 (2,q, OCH2 methyl), 3.80 (q, 2, OCH2), 4.00(q, 2, OCH2), 5.05–5.25 (m, 4, CH2 vinyl), 5.90–6.20 (m, 2, CH vinyl), 7.05–7.20 (m, 4, CH2 vinyl), 7.05–7.20 (m, 3, aromatic). Oxidation of the product as described in Example 1 gave 2,6-di-(2,3-epoxypropyl)phenyl ethoxyethyl ether as an oil. MS m/z 278 (M+ calcd for C16H22O4=278). H NMR (300 MHz, CDCl3) d 1.25 (t, 3, CH30, 2.65–2.85 (m, 4, epoxypropyl CH2), 2.90–3.15 (m, 4, epoxypropyl CH2), 3.21–3.35(m, 2, epoxypropyl CH), 3.65 (q, 2, OCH2), 3.80 (q, 2, OCH2), 4.00 (q, 2, OCH2), 5.33 (s, 3, OCH3), 7.05–7.33 (m, 3, aromatic).
