2-Chloroethanol → 2-(4-Iodophenoxy)ethanol

HRID 981145

Reaction equation

HRID 981145 reaction equation
[Na].[I:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.Cl[CH2:11][CH2:12][OH:13].[Cl-].[NH4+]>C(O)C>[I:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:11][CH2:12][OH:13])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 342-ChloroethanolHCID 108944-IodophenolHCID 25517Ammonium ChlorideHCID 5360545Sodium

Product 1

HCID 35132082-(4-Iodophenoxy)ethanolYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium (0.53 g) was dissolved in ethanol (50 ml) under nitrogen and 4-iodophenol (5.0 g), and 2-chloroethanol (3.93 g), were added successively. The mixture was refluxed for 18 h, treated with saturated aqueous ammonium chloride (50 ml) and evaporated. The aqueous residue was extracted with ER (3×100 ml) and the dried extract was evaporated onto silica (Merck 9385; 50 ml) and purified by [C] eluted with cyclohexane-ER (7:3) followed by cyclohexane-ER (1:1) to give the title compound (3.0 g) m.p. 76°-77°.

Workup

  1. temperatureThe mixture was refluxed for 18 h
  2. customevaporated
  3. extractionThe aqueous residue was extracted with ER (3×100 ml)
  4. extractionthe dried extract
  5. customwas evaporated onto silica (Merck 9385; 50 ml)
  6. custompurified by [C]
  7. washeluted with cyclohexane-ER (7:3)

Sources & evidence

ORD record
ord-bb88b4021fb443c68845c639338c7086
Source dataset
uspto-grants-1991_02
Patent number
US04990505

Linked notes

Loading…