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

HRID 52761Notes

Reaction equation

HRID 52761 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 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##

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 layer was dried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-c080f9c38172419eb9115be300545e76
Source dataset
uspto-grants-1997_04
Patent number
US05616729

Reaction notes

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