Reaction #46188

Reaction equation

Na2CO3

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

HCl

→

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

Yield 43.1%

Solvents

water

Conditions

Workup

1. 1
   Extractionextracted with EtOAc (200 mL×3)
2. 2
   WashThe organic layer was washed with brine
3. 3
   Dryingdried over anhydrous Na2SO4
4. 4
   Otherevaporated under vacuum
5. 5
   Otherto give crude product, which
6. 6
   Otherwas purified by column (Petroleum Ether/EtOAc 15:1)

Procedure

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).

Source