HCID 13343709, compound → HCID 13343699, compound

Participants

Reaction Steps

To a solution of (16i) (29 g., 0.14 mole) dissolved in aqueous sodium hydroxide (15 g. NaOH in 750 ml. of water) was added 550 g. of 5% sodium amalgam portionwise over a period of 30 minutes. The mixture was stirred for 5 hours and then decanted from the mercury and filtered through Celite. The filtrate was acidified with hydrochloric acid and cooled in an ice bath. There was obtained 26 g. of crude acid after filtering. Recrystallization from methylene chloride/hexane gave pure 2,3-dihydro-6-methoxy-7-methylbenzofuran-2-carboxylic acid, m.p. 142°-143° C. Esterification of this material by the procedure described in Example 35 gave (5i) as an oil. Analysis (C13H16O4) C,H.

Provenance & Evidence