Allyl Alcohol → 3-(4-(Hydroxymethyl)phenyl)propanal

HRID 271635

Reaktionsgleichung

Reaktionsgleichung von HRID 271635
[CH2:1]([OH:4])[CH:2]=[CH2:3].C([O-])(O)=O.[Na+].I[C:11]1[CH:18]=[CH:17][C:14]([CH2:15][OH:16])=[CH:13][CH:12]=1.CCOC(C)=O>O.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2].O>[OH:16][CH2:15][C:14]1[CH:17]=[CH:18][C:11]([CH2:3][CH2:2][CH:1]=[O:4])=[CH:12][CH:13]=1

Komponenten

9

Edukt 4

HCID 7858Allyl AlcoholHCID 8857Ethyl AcetateHCID 290124-Iodobenzyl alcoholHCID 516892Sodium Bicarbonate

Produkt 1

HCID 534252763-(4-(Hydroxymethyl)phenyl)propanal

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 167845palladium(II) acetateKatalysatorHCID 16212273Tetrabutylammonium chloride hydrateKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

10.5 mL (152.8 mmol) allylalcohol, 18.8 g (62.2 mmol) Tetrabutylammonium chloride monohydrate, 12.8 g (152.8 mmol) NaHCO3 and 0.75 g (3.1 mmol) Pd(OAc)2 is added to a solution of 15.0 g (62.2 mmol) 4-iodobenzylalcohol in 100 mL DMF at RT under an N2 atmosphere and the reaction solution is heated to 60° C. for 3 h. The solvent is eliminated i.vac., the residue combined with 250 mL EtOAc and 80 mL water and suction filtered through a fibreglass filter. 80 mL NaCl solution are added to the filtrate, the phases are separated and the organic phase is dried over MgSO4. After the desiccant and solvent have been eliminated the residue is purified by column chromatography on silica gel (gradient: cyc/EtOAc 3:1 after cyc/EtOAc 1:1).

Aufarbeitung

  1. filtrationfiltered through a fibreglass
  2. filtrationfilter
  3. addition80 mL NaCl solution are added to the filtrate
  4. customthe phases are separated
  5. dry with materialthe organic phase is dried over MgSO4
  6. customis purified by column chromatography on silica gel (gradient: cyc/EtOAc 3:1 after cyc/EtOAc 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-c091aec98fb744dc835629a691d3c1bb
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452911B2

Verknüpfte Notizen

Wird geladen…