Hydrochloric Acid → 2-(4-Iodophenoxy)ethanol

HRID 343565

Reaktionsgleichung

Reaktionsgleichung von HRID 343565
[C:1]1(=O)[O:5][CH2:4][CH2:3][O:2]1.[I:7][C:8]1[CH:13]=[CH:12]C(O)=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+].Cl.[OH-].[Na+]>>[OH:5][CH2:4][CH2:3][O:2][C:1]1[CH:12]=[CH:13][C:8]([I:7])=[CH:9][CH:10]=1

Komponenten

6

Edukt 5

HCID 313Hydrochloric AcidHCID 7303Ethylene carbonateHCID 108944-IodophenolHCID 11430Potassium Carbonate2×HCID 14798Sodium Hydroxide

Produkt 1

HCID 35132082-(4-Iodophenoxy)ethanolAusbeute 27 %

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A melt of ethylene carbonate (6.5 g, 74 mmol) in a small flask under Argon was treated with 4-iodophenol (0.400 g, 1.82 mmol) and powdered potassium carbonate (1.26 g, 9.1 mmol) and was stirred at 90° C. for 3 hr. The mixture was treated with cold dilute hydrochloric acid to decompose the excess potassium carbonate and excess aqueous sodium hydroxide solution was slowly added and the mixture was stirred over night. The suspension was extracted with methylene chloride, was washed with water and brine, was dried over sodium sulfate and was stripped to afford a white solid, which was purified by flash chromatography on silica gel (20 mL) with methylene chloride to afford (0.128 g, 27%) of the titled intermediate as a white solid, mp 76°-77.5° C.

Aufarbeitung

  1. additionwas slowly added
  2. stirringthe mixture was stirred over night
  3. extractionThe suspension was extracted with methylene chloride
  4. washwas washed with water and brine
  5. dry with materialwas dried over sodium sulfate
  6. customto afford a white solid, which
  7. customwas purified by flash chromatography on silica gel (20 mL) with methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-2b2efe22dbd0427d9cf24b213a8634f8
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05861421

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