Reaktion #75795

Reaktionsgleichung

phenyl magnesium bromide

methyl 4-formylbenzoate

→

methyl 4-(α-hydroxybenzyl)benzoate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeit was quenched by the addition of 1 M hydrochloric acid (125 mL)
2. 2
   ExtraktionThe reaction mixture was extracted with diethyl ether (2×200 mL)
3. 3
   WaschenThe combined extracts were washed with brine
4. 4
   Trocknendried over magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated under vacuum
7. 7
   Sonstigeto provide a yellow oil
8. 8
   SonstigeThis material was purified by flash chromatography (silica gel eluting with 6:1 hexanes:ethyl acetate)

Vorschrift

Under a nitrogen atmosphere phenyl magnesium bromide (39 mL of 3 M in ether) was added via a syringe over a period of 30 minutes to a solution of methyl 4-formylbenzoate (19.2 g, 117 mmol). The mixture was allowed to stir for an additional 10 minutes and then it was quenched by the addition of 1 M hydrochloric acid (125 mL). The reaction mixture was extracted with diethyl ether (2×200 mL). The combined extracts were washed with brine, dried over magnesium sulfate, filtered and then concentrated under vacuum to provide a yellow oil. This material was purified by flash chromatography (silica gel eluting with 6:1 hexanes:ethyl acetate) to provide 6.9 g of methyl 4-(α-hydroxybenzyl)benzoate as a clear oil.

Quelle