Reaktion #985634

Reaktionsgleichung

2-Allyl-4-benzyloxyphenol

hydrogen

→

solid

Ausbeute 56.0%

4-Benzyloxy-2-propylphenol

Ausbeute 56.0%

Lösungsmittel

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe mixture was filtered
2. 2
   Einengenconcentrated
3. 3
   SonstigeThe crude product was purified on a Biotage medium pressure chromatography system
4. 4
   Wascheneluted with 10% ethyl acetate in hexanes

Vorschrift

2-Allyl-4-benzyloxyphenol (WO 9728137 A1 19970807, Adams, A. D. et al.) (5.00 g, 20.8 mmol) in ethyl acetate (40 mL) was treated with 5% Pd/C (0.25 g) and hydrogen (1 atm) at ambient temperature for 18 h. The mixture was filtered and concentrated. The crude product was purified on a Biotage medium pressure chromatography system using a 40 L normal phase cartridge and eluted with 10% ethyl acetate in hexanes to give a tan solid (2.8 g, 56%). Rf=0.33 (25% EtOAc/Hexanes); 1H NMR (400 MHz, CDCl3) δ 7.44-7.31 (m, 5H), 6.78 (s, 1H), 6.69 (d, J=1.5 Hz, 2H), 5.00 (s, 2H), 4.31 (s, 1H), 2.55 (t, J=7.6 Hz, 2H), 1.64 (q, J=7.5 Hz, 2H), 0.97 (t, J=7.3 Hz, 3H).

Quelle