反应详情

A mixture of 2,6-di-t-butylphenol (1 g) in trifluoroacetic anhydride (5 ml) is carefully treated with 0.28 ml of glacial acetic acid and the reaction mixture is stirred at 20°-25° for 1 hr. The reaction mixture is diluted with chloroform and is separated, washed with saline, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product (1.39 g) is chromatographed on 180 g of silica gel. The column is packed and eluted with chloroform/acetone (99/1). An initial fraction of 200 ml is collected, followed by 7 ml fractions. Based on their TLC homogeniety, fractions 20-55 are combined and concentrated. Recrystallized from hexane gives the tire compound, mp 148°-150°; IR (mineral oil) 3581, 3007, 2956, 2925, 2871, 2856, 1663, 1596, 1581, 1465, 1463, 1442, 1423, 1370, 1364, 1356, 1320, 1305, 1274, 1239, 1232, 1138, 1124, 1108 an 886 cm-1 ; NMR (CDCl3, TMS) 7.84, 5.73, 2.56, and 1.47δ; CMR (CDCl3, TMS) 197.6, 158, 4, 135.8, 129.1, 126.1, 34.4, 30.2 and 26.3δ; MS (m/z) M+ (found)=248; other ions at m/z 233, 217, 205, 189, 178, 115, 57 and 43.

1. customis separated
2. washwashed with saline
3. dry with materialdried over anhydrous sodium sulfate
4. concentrationconcentrated under reduced pressure
5. customThe crude product (1.39 g) is chromatographed on 180 g of silica gel
6. washeluted with chloroform/acetone (99/1)
7. customAn initial fraction of 200 ml is collected
8. concentrationconcentrated
9. customRecrystallized from hexane
10. customgives the tire compound, mp 148°-150°