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Preparation of gem
-Diacetates: A mixture of aldehyde (5 mmol) freshly distilled acetic anhydride (5 mmol) and LiBF4 (5 mmol) in acetonitrile (15 mL) was stirred at r.t. for an appropriate time (Table). After complete conversion, as indicated by TLC, the reaction mixture was poured into sat. sodium bicarbonate solution (30 mL) and extracted with ethyl acetate (2 × 15 mL). The combined organic layers were dried over anhyd Na2SO4 and concentrated in vacuo. The resulting product was recrystallized from ethyl acetate-hexane (2:8) to afford pure 1,1-diacetate.
Spectral data. 3b: Solid, mp 72-74 °C, 1H NMR (CDCl3): δ = 2.18 (s, 6 H), 3.88 (s, 3 H), 3.89 (s, 3 H), 6.83 (d, 1 H, J = 8.0 Hz), 7.03 (s, 1 H), 7.08 (d, 1 H, J = 8.0 Hz), 7.58 (s, 1 H). MS (EI): m/z = 268 [M+], 167, 139, 95, 77, 43. IR (KBr): 3049, 2955, 1745, 1687, 1495, 1243, 1010, 968
cm-1. 3d: Solid, mp 66-67 °C (ref.
[6]
66-67). 1H NMR (CDCl3): δ = 2.15 (s, 6 H), 7.10 (dd, 1 H, J = 5.0, 4.5 Hz), 7.30 (d, 1 H, J = 4.5 Hz), 7.40 (d, 1 H, J = 5.0 Hz), 7.90 (s, 1 H). MS (EI): m/z = 214 [M+], 171, 155, 112, 85. IR(neat): 3050, 2960, 1757, 1480, 1245, 1017, 845 cm-1. 3f: Solid, mp 84-85 °C (ref.
[5]
84-86). 1H NMR (CDCl3): δ = 2.15 (s, 6 H), 5.95 (dd, 1 H, J = 16.5 and 7.2 Hz), 6.85 (d, 1 H, J = 16.5 Hz), 7.20-7.45 (m, 6 H). MS (EI): m/z = 234 [M+], 191, 175, 132, 101, 91. IR (KBr): 3055, 2955, 1750, 1680, 1490, 1240, 1015, 970 cm-1. 3h: 1H NMR (CDCl3): δ = 2.20 (s, 6 H), 7.80 (t, 2 H, J = 8.2 Hz), 7.60 (s, 1 H), 7.65 (m, 1 H), 7.95 (d, 2 H, J = 8.2 Hz). MS (EI): m/z = 236 [M+], 193, 105, 77, 51, 43. IR (KBr): 3055, 2970, 1760, 1720, 1235, 1020 cm-1. 3i: 1H NMR (CDCl3): δ = 2.16 (s, 6 H), 6.98-7.05 (m, 3 H), 7.08-7.20 (m, 3 H), 7.30-7.38 (m, 3 H), 7.60 (s, 1 H). MS (EI): m/z = 300 [M+], 198, 170, 142, 115, 77, 43. IR (KBr): 3053, 2965, 1748, 1680, 1490, 1240, 1015, 967 cm-1. 3k: Liquid, 127-129/2mm (ref.
[6]
128/2mm). 1H NMR (CDCl3): δ = 0.95 (t, 3 H, J = 6.8 Hz), 1.25-1.50 (m, 6 H), 1.75-1.83 (m, 2 H), 2.15 (s, 6 H), 6.70 (t, 1 H, J = 6.8 Hz). MS (EI):
m/z = 202 [M+], 159, 143, 100, 84. IR(neat): 3040, 2955, 1750, 1685, 1485, 1245, 1020, 965 cm-1.