Sodium Iodide → 4-[4-(2-Hydroxyethoxy)phenyl]butan-2-one

HRID 851183Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 851183
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10](=[O:12])[CH3:11])=[CH:4][CH:3]=1.Br[CH2:14][CH2:15][OH:16].[OH-].[Na+].[I-].[Na+]>O>[OH:16][CH2:15][CH2:14][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10](=[O:12])[CH3:11])=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 108982-BromoethanolHCID 14798Sodium HydroxideHCID 216484-(4'-Hydroxyphenyl)-2-butanone

Produkt 1

HCID 130796444-[4-(2-Hydroxyethoxy)phenyl]butan-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 4-[4-hydroxyphenyl]butan-2-one (16.4 g], 2-bromoethanol (16.9 g), sodium hydroxide (7.5 g), sodium iodide (7.5 g) and water (200 ml) was heated under reflux for 4 hours, cooled and extracted with dichloromethane. The extract was washed with brine, dried (MgSO4) and evaporated to dryness. The residual oil was distilled to give the title compound as a colourless liquid, bp 170°-1°/0.8 mm. P τ(CDCl3) 7.85 (3H, s), 7.15-7.35 (4H, complex), 7.4-7.6 (1H, t), 5.85-6.25 (4H, complex), 2.8-3.4 (4H, dd).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. temperaturecooled
  4. extractionextracted with dichloromethane
  5. washThe extract was washed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated to dryness
  8. distillationThe residual oil was distilled

Quellen und Nachweise

ORD-Eintrag
ord-802e2da9209748e99c0483369113dc5c
Quelldatensatz
uspto-grants-1983_05
Patentnummer
US04382958

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