Reaction #81039

Reaction equation

Sodium iodide

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

ethyl acetate hexane

→

product

Yield 102.9%

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

Yield 102.9%

Solvents

acetone

Conditions

Workup

1. 1
   Temperaturerefluxed for 6 days
2. 2
   Otherafter the completion of reaction, solvent
3. 3
   Otherwas evaporated
4. 4
   Otherto obtain a white solid
5. 5
   WashThis solid was washed with methylene chloride several times
6. 6
   Washthe combined organic layers were again washed with water
7. 7
   DryingThe organic layer was dried over MgSO4
8. 8
   Concentrationconcentrated

Procedure

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