1-Bromo-3,5-dimethyladamantane → 3,5-dimethyl-1-adamantyl Acetate
Reaction equation
[CH3:1][C:2]12[CH2:12][CH:6]3[CH2:7][C:8]([CH3:11])([CH2:10][C:4](Br)([CH2:5]3)[CH2:3]1)[CH2:9]2.[C:14]([O-:17])(=[O:16])[CH3:15].[K+]>C(O)(=O)C>[C:14]([O:17][C:4]12[CH2:3][C:2]3([CH3:1])[CH2:12][CH:6]([CH2:7][C:8]([CH3:11])([CH2:9]3)[CH2:10]1)[CH2:5]2)(=[O:16])[CH3:15]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
2.486 (10.2 mmoles) of 3,5-dimethyl-1-bromoadamantane is refluxed for 16 hours with 2.034 g (20.7 mmoles) of potassium acetate in 10 mL of acetic acid. The solution is poured over 100 grams of ice, allowed to melt, and extracted with 3×10 mL of diethyl ether. The combined ether extracts are washed with saturated aqueous sodium bicarbonate followed by saturated aqueous sodium chloride, then dried over sodium sulfate. The solvent is removed under vacuum, yielding 1.521 (67%) of the desired product, a colorless oil. TLC: Rf=0.68 (silica plate: eluant hexane 90%, ethyl acetate 10%). 1HNMR (CDCl3, 500 Mhz): 0.858 (s, 6H), 1.115 (d, 2H, J=12.4 Hz), 1.177 (d, 2H, J=12.4 Hz), 1.260 (d, 2H, J=12.3 Hz), 1.367 (d, 2H, J=12.3 Hz), 1.714 (d, 2H, J=11.6 Hz), 1.766 (d, 2H, J=11.6 Hz), 1.939 (s, 2H), 1.976 (s, 3H), 2.191 (m, 1H).