Reaktion #81039

Reaktionsgleichung

Sodium iodide

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

ethyl acetate hexane

→

product

Ausbeute 102.9%

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

Ausbeute 102.9%

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturrefluxed for 6 days
2. 2
   Sonstigeafter the completion of reaction, solvent
3. 3
   Sonstigewas evaporated
4. 4
   Sonstigeto obtain a white solid
5. 5
   WaschenThis solid was washed with methylene chloride several times
6. 6
   Waschenthe combined organic layers were again washed with water
7. 7
   TrocknenThe organic layer was dried over MgSO4
8. 8
   Einengenconcentrated

Vorschrift

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##

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