Reacción #46188

Ecuación de reacción

Na2CO3

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

HCl

→

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

Rendimiento 43.1%

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with EtOAc (200 mL×3)
2. 2
   LavadoThe organic layer was washed with brine
3. 3
   Secadodried over anhydrous Na2SO4
4. 4
   Otroevaporated under vacuum
5. 5
   Otroto give crude product, which
6. 6
   Otrowas purified by column (Petroleum Ether/EtOAc 15:1)

Procedimiento

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).

Fuente