تفاعل #46188

معادلة التفاعل

Na2CO3

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

HCl

→

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

المردود 43.1%

المذيبات

water

ظروف التفاعل

المعالجة

1. 1
   استخلاصextracted with EtOAc (200 mL×3)
2. 2
   غسيلThe organic layer was washed with brine
3. 3
   تجفيفdried over anhydrous Na2SO4
4. 4
   أخرىevaporated under vacuum
5. 5
   أخرىto give crude product, which
6. 6
   أخرىwas purified by column (Petroleum Ether/EtOAc 15:1)

الإجراء التجريبي

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).

المصدر