Acrylonitrile → HCID 20383063, compound

Participants

Reaction Steps

To a stirred, refluxing mixture of 50 g of 3-chloro-6-hydroxybenzaldehyde and 62 ml of acrylonitrile in 50 ml of water was added dropwise over a three-hour period a solution of 12.8 g of sodium hydroxide in 120 ml of water. Then an additional 62 ml of acrylonitrile was added and the stirred mixture was refluxed for 2 hours, then allowed to stand at room temperature overnight. The crystals which formed were filtered off, washed with water and dried to give a solid, which was recrystallized from ethanol to give 6-chloro-3,4-dihydro-4-hydroxy-(2H)-1-benzopyran-3-carbonitrile (6A), a solid. A mixture of 6A with 250 ml of methanol containing 2 ml of sulfuric acid was refluxed for 4 days and stripped of solvent. The resulting residue was dry column chromatographed over silica gel, using Solvent No. 3 as eluent. The product obtained on workup was rechromatographed and recrystallized from ether to give methyl 6-chloro-2H-1-benzopyran-3-carboxylate (6B), as light yellow needles, mp: 106°-109° C.

Provenance & Evidence