4-Hydroxybenzaldehyde → 4-(2,2,3,3,3-Pentafluoropropoxy)benzaldehyde

HRID 1046290

Reaktionsgleichung

Reaktionsgleichung von HRID 1046290
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].CC1C=CC(S(O[CH2:27][C:28]([F:34])([F:33])[C:29]([F:32])([F:31])[F:30])(=O)=O)=CC=1>CN(C=O)C.C(OCC)(=O)C>[F:33][C:28]([F:34])([C:29]([F:32])([F:31])[F:30])[CH2:27][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 27760172,2,3,3,3-Pentafluoropropyl p-Toluenesulfonate

Produkt 1

HCID 866134424-(2,2,3,3,3-Pentafluoropropoxy)benzaldehydeAusbeute 30,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 4-hydroxybenzaldehyde (2 g, 16.7 mmol) in DMF (33 mL) was stirred as solid potassium carbonate (4.1 g, 29.7 mmol) was added, and the reaction mixture was then stirred at RT. After 30 min, solid 2,2,3,3,3-pentafluoropropyl 4-methylbenzenesulfonate (5 g, 16.4 mmol) was added into the reaction mixture. The mixture was stirred and heated at 100° C. for 7 h. The reaction mixture was allowed to cool, diluted with ethyl acetate, washed with water (3×) and brine, and concentrated. Purification by flash chromatography on silica gel using a gradient of ethyl acetate in hexane afforded 4-(2,2,3,3,3-pentafluoropropoxy)benzaldehyde (1.26 g).

Aufarbeitung

  1. additionwas added
  2. stirringThe mixture was stirred
  3. temperatureheated at 100° C. for 7 h
  4. temperatureto cool
  5. washwashed with water (3×) and brine
  6. concentrationconcentrated
  7. customPurification by flash chromatography on silica gel using a gradient of ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-4cf4c35a19d84aa797f46e06d93bf515
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569303B2

Verknüpfte Notizen

Wird geladen…