Sodium Methoxide → 6-Chloro-3-hydroxy-1-benzofuran-2-carbonitrile
Reaction equation
[C:1]([C:5]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:6]=1[O:7][CH2:8][C:9]#[N:10])(OC)=[O:2].C[O-].[Na+]>C1C=CC=CC=1>[Cl:15][C:12]1[CH:13]=[CH:14][C:5]2[C:1]([OH:2])=[C:8]([C:9]#[N:10])[O:7][C:6]=2[CH:11]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 2-(2-carbomethoxy-5-chlorophenoxy)acetonitrile (22.6 g, 0.1 mol, described in Example 2) and sodium methoxide (0.2 mol, prepared from 4.6 g sodium metal and 50 mL dry methanol) in benzene (400 mL) was stirred and refluxed for 2 hr. After cooling, the precipitate was collected and dissolved in water. The solution was acidified with concentrated hydrochloric acid. The precipitate was extracted into diethyl ether and the solution was dried and evaporated. The solid residue was triturated with petroleum ether and gave 19.0 g of the title compound: mp ca 205° C., and NMR (DMSO-d6) δ7.6 (3H,m), and 11.4 (1H, broad).