Reaktion #546340

Reaktionsgleichung

HCl

4-[1,3]dioxolan-2-yl-2-fluoro-phenol

→

3-Fluoro-4-hydroxy-benzaldehyde

Ausbeute 95.2%

Lösungsmittel

water

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with methylene chloride (4×10 mL)
2. 2
   TrocknenThe combined organic layers were dried (Na2SO4)
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated under vacuum
5. 5
   SonstigeThe residue was chromatographed (silica gel, hexanes/ethyl acetate 1:1)

Vorschrift

A solution of 1N HCl (1 mL) and 4-[1,3]dioxolan-2-yl-2-fluoro-phenol (250 mg, 1.35 mmol) in THF (2 mL) was stirred, at room temperature for 1 hour. The mixture was diluted with water and extracted with methylene chloride (4×10 mL). The combined organic layers were dried (Na2SO4), filtered and concentrated under vacuum. The residue was chromatographed (silica gel, hexanes/ethyl acetate 1:1) to produce 3-Fluoro-4-hydroxy-benzaldehyde as a white solid (180 mg, 95%). 1H-NMR (CDCl3, 200.15 MHz): 9.84 (d, 1H, J=2.4), 7.68–7.59 (m, 2H), 7.15 (t, 1H, J=8.5), 6.5 (sa, 1H).

Quelle