Sodium borohydride → 4-Chloro-2,6-dimethylbenzyl alcohol
Reaktionsgleichung
[Cl:1][C:2]1[CH:9]=[C:8]([CH3:10])[C:5]([CH:6]=[O:7])=[C:4]([CH3:11])[CH:3]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH3:11])[C:5]([CH2:6][OH:7])=[C:8]([CH3:10])[CH:9]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
Dissolve 4-chloro-2,6-dimethyl benzaldehyde (5.0 g, 168.64 g/mol) in 100 mL dry methanol. Cool to 0° C. while stirring under N2. Portionwise add powdered NaBH4 (0.76g, 37.85 g/mol) over 5 minutes. Stir at 0° C. for 2 hours, monitoring by TLC until aldehyde consumed, then evaporate to a yellow oil. Add H2O (50 mL) and bring to pH. 7.0 by addition of saturated NH4Cl. Extract the neutral aqueous layer with CH2Cl2 (3×75 mL) and dry the pooled organic layers over Na2SO4. Filter and concentrate to a yellow oil. Flush through a pad of silica to remove baseline material, then evaporate to a yellow solid (3.0 g) which can be used without further purification. LCMS=171.6 (MH+), 169.6 (M−)