Water → 2,6-Diethyl-4-methylbenzyl alcohol

HRID 385238Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 385238
[CH2:1]([C:3]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH2:12][CH3:13])[C:4]=1[CH:5]=[O:6])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.S(=O)(=O)(O)O>C(OCC)C>[CH2:1]([C:3]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH2:12][CH3:13])[C:4]=1[CH2:5][OH:6])[CH3:2]

Komponenten

6

Edukt 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 21226445Aluminium lithium hydrideHCID 221537982,6-Diethyl-4-methylbenzaldehyde

Produkt 1

HCID 667075402,6-Diethyl-4-methylbenzyl alcoholAusbeute 92,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

A solution of 35.5 g (201.4 mmol) of 2,6-diethyl-4-methylbenzaldehyde, dissolved in 80 ml of diethyl ether is added dropwise to a suspension of 2.10 g (55.4 mmol) of lithium aluminium hydride in 200 ml of diethyl ether. The mixture is then heated at reflux for another 1 h. After cooling, the mixture is hydrolyzed with water and 10% strength sulphuric acid, the phases are separated and the aqueous phase is extracted two more times with diethyl ether. Drying (magnesium sulphate), distillative removal of the solvent and chromatography of the resulting crude product on silica gel (ethyl acetate/hexane=30:70) gives 33.10 g (92%) of 2,6-diethyl-4-methylbenzyl alcohol in the form of colourless crystals of m.p. 71-72° C. 1H-NMR (400 MHz, CDCl3): δ=1.22 (t, 6H), 2.30 (s, 3H), 2.74 (q, 4H), 4.71 (s, 2H), 6.90 (s, 2H).

Aufarbeitung

  1. temperatureThe mixture is then heated
  2. temperatureat reflux for another 1 h
  3. temperatureAfter cooling
  4. customthe phases are separated
  5. extractionthe aqueous phase is extracted two more times with diethyl ether
  6. customDrying
  7. custom(magnesium sulphate), distillative removal of the solvent and chromatography of the resulting crude product on silica gel (ethyl acetate/hexane=30:70)

Quellen und Nachweise

ORD-Eintrag
ord-78777e775d634ce1bb2c4aa1c76e2e94
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367873B2

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