Réaction #81039

Équation de réaction

Sodium iodide

[(2-chloroethoxy)(3-hydroxyphenyl)methylene]adamantane

ethyl acetate hexane

→

product

Rendement 102.9%

[(3-Hydroxyphenyl)(2-iodoethoxy)methylene]adamantane

Rendement 102.9%

Solvants

acetone

Conditions de réaction

Traitement

1. 1
   Températurerefluxed for 6 days
2. 2
   Autreafter the completion of reaction, solvent
3. 3
   Autrewas evaporated
4. 4
   Autreto obtain a white solid
5. 5
   LavageThis solid was washed with methylene chloride several times
6. 6
   Lavagethe combined organic layers were again washed with water
7. 7
   SéchageThe organic layer was dried over MgSO4
8. 8
   Concentrationconcentrated

Mode opératoire

Sodium iodide (14.0 g, 0.09 mol) and [(2-chloroethoxy)(3-hydroxyphenyl)methylene]adamantane (3.0 g, 0.009 mol) were dissolved in dry acetone and refluxed for 6 days. The reaction was followed by TLC analysis (silica gel, 10% ethyl acetate/hexane) and after the completion of reaction, solvent was evaporated to obtain a white solid. This solid was washed with methylene chloride several times and the combined organic layers were again washed with water. The organic layer was dried over MgSO4 and concentrated to give 3.8 g (100%) of product as an oily material: 1H NMR (CDCl3) δ 1.78-1.97 (m, 12H), 2.64 (bs, 1H), 3.19 (t, 2H, J=7.1 MHz), 3.35 (bs, 1H), 3.69 (t, 2H, J=7.1 MHz), 6.75-7.21 (m, 4H); 13C NMR (CDCl3) δ 2.40, 28.13, 30.41, 32.33, 36.99, 38.86, 39.09, 69.74, 114.86, 116.00, 121.79, 129.28, 133.37, 136.42, 140.51, 155.66. MS m/e (rel intensity) 410 (42), 256 (19), 227 (75), 155 (18), 121 (100), 107 (32), 93 (28), 79 (14), 65 (16); Exact mass: calcd 410.0744, found: 410.0744. ##STR32##

Source