Sodium Hydroxide → 7-Chloro-3(2H)-benzofuranone
Reaction equation
C([C:5]1[O:6][C:7]2[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][C:8]=2[C:9]=1[OH:10])(OC)=O.[OH-].[Na+]>O1CCOCC1>[Cl:15][C:14]1[C:7]2[O:6][CH2:5][C:9](=[O:10])[C:8]=2[CH:11]=[CH:12][CH:13]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
According to the procedure of D. C. Schroeder, et al., J Org. Chem., 27, 586 (1962) a mixture of 2-carbomethoxy-7-chloro-3-hydroxybenzofuran (16.9 g, 0.075 mol), dioxane 75 mL), and 1N NaOH (375 mL, 0.375 mol) was stirred at room temperature for 2 days. The dioxane was removed under reduced pressure and the mixture was left standing for another day. Acidification with 2N HCl (270 mL, slowly) and filtration of the resulting precipitate gave a yellow solid (12.6 g). NMR analysis showed this material to be a 3:1 mixture of product and starting material. Purification by preparative HPLC gave a yellow solid (5.8 g, 46%), m.p. 108°-111° C.