Sodium Iodide → [(3-Hydroxyphenyl)(2-iodoethoxy)methylene]adamantane

HRID 1940365Notes

Reaction equation

HRID 1940365 reaction equation
[I-:1].[Na+].Cl[CH2:4][CH2:5][O:6][C:7](=[C:15]1[CH:22]2[CH2:23][CH:18]3[CH2:19][CH:20]([CH2:24][CH:16]1[CH2:17]3)[CH2:21]2)[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([OH:14])[CH:9]=1.C(OCC)(=O)C.CCCCCC>CC(C)=O>[OH:14][C:10]1[CH:9]=[C:8]([C:7](=[C:15]2[CH:22]3[CH2:23][CH:18]4[CH2:19][CH:20]([CH2:24][CH:16]2[CH2:17]4)[CH2:21]3)[O:6][CH2:5][CH2:4][I:1])[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 15158794[(2-Chloroethoxy)(3-hydroxyphenyl)methylene]adamantaneHCID 21226206Ethyl acetate hexane

Product 1

HCID 15158795[(3-Hydroxyphenyl)(2-iodoethoxy)methylene]adamantaneYield 102.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

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 Tayer was dried over MgSO4 and concentrated to give 3.8 g (100%) of product as an oily material. 1H NMR (CDCl3) δ1.78-1.97 (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) δ2.40, 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. ##STR31##

Workup

  1. temperaturerefluxed for 6 days
  2. customafter the completion of reaction, solvent
  3. customwas evaporated
  4. customto obtain a white solid
  5. washThis solid was washed with methylene chloride several times
  6. washthe combined organic layers were again washed with water
  7. dry with materialThe organic Tayer was dried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-61e577e5acf345b0842968ddc4c6992a
Source dataset
uspto-grants-1997_12
Patent number
US05698728

Reaction notes

Loading…