Reaktion #46188

Reaktionsgleichung

Na2CO3

1-(3-chloromethyl-4-methoxy-phenyl)-cyclopropanecarboxylic acid methyl ester

HCl

→

1-(3-hydroxymethyl-4-methoxy-phenyl)-cyclopropanecarboxylic acid methyl ester

Ausbeute 43.1%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with EtOAc (200 mL×3)
2. 2
   WaschenThe organic layer was washed with brine
3. 3
   Trocknendried over anhydrous Na2SO4
4. 4
   Sonstigeevaporated under vacuum
5. 5
   Sonstigeto give crude product, which
6. 6
   Sonstigewas purified by column (Petroleum Ether/EtOAc 15:1)

Vorschrift

To a suspension of crude 1-(3-chloromethyl-4-methoxy-phenyl)-cyclopropanecarboxylic acid methyl ester (20.0 g) in water (350 mL) was added Bu4NBr (4.0 g) and Na2CO3 (90.0 g, 0.85 mol) at room temperature. The reaction mixture was heated at 65° C. overnight. The resulting solution was acidified with aq. HCl (2 mol/L) and extracted with EtOAc (200 mL×3). The organic layer was washed with brine, dried over anhydrous Na2SO4 and evaporated under vacuum to give crude product, which was purified by column (Petroleum Ether/EtOAc 15:1) to give 1-(3-hydroxymethyl-4-methoxy-phenyl)-cyclopropanecarboxylic acid methyl ester (8.0 g, 39%). 1H NMR (CDCl3, 400 MHz) δ 7.23-7.26 (m, 2H), 6.83 (d, J=8.0 Hz, 1H), 4.67 (s, 2H), 3.86 (s, 3H), 3.62 (s, 3H), 1.58 (q, J=3.6 Hz, 2H), 1.14-1.17 (m, 2H).

Quelle