Hydrochloric Acid → 3,4-dihydro-2,5-dimethyl-8-nitro-2H-1-benzopyran

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Reaction Steps

40.5 g of 1C was added in portions over 20 minutes to a stirred mixture of 3.4 g of sodium hydride in 300 ml of DMSO at room temperature, and the resulting mixture was stirred for 18 hours at room temperature. The mixture was poured into ice water, made slightly acidic with concentrated hydrochloric acid and filtered. The solid was dried to give 3,4-dihydro-2,5-dimethyl-8-nitro-2H-1-benzopyran (1D) as a yellow solid, m.p.: 83°-85° C.

Provenance & Evidence