3-Iodophenol → HCID 18008068, compound

HRID 988244Notes

Reaction equation

HRID 988244 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[OH-].[K+].Br[CH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=1>C(O)C>[I:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][CH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=1

Participants

5

Reactant 3

HCID 122723-IodophenolHCID 14797Potassium HydroxideHCID 703202-Bromomethylnaphthalene

Product 1

HCID 18008068HCID 18008068, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-iodophenol (4.0 g, 18 mmol) in ethanol (40 mL) is added potassium hydroxide (1.0 g, 18 mmol) and 2-(bromomethyl) naphthalene (4.0 g, 18 mmol) and this mixture is refluxed overnight. The hot reaction is filtered and the filtrate is chilled in ice. The ensuing precipitate is collected by filtration to give the title compound. 1H NMR (300 MHz, CDCl3) δ 7.84-7.89 (m, 4H), 7.48-7.53 (m, 3H), 7.40 (d, 1H), 7.29-7.32 (m, 1H), 6.95-7.04 (m, 2H), 5.20 (s, 2H); MS (EI) 360 (M)+.

Workup

  1. temperaturethis mixture is refluxed overnight
  2. customThe hot reaction
  3. filtrationis filtered
  4. temperaturethe filtrate is chilled in ice
  5. filtrationThe ensuing precipitate is collected by filtration

Sources & evidence

ORD record
ord-1ab441ee83b64e6db2c04f589f1b7230
Source dataset
uspto-grants-2003_10
Patent number
US06635655B1

Reaction notes

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