4-Chlororesorcinol → 6-Chloro-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-7-ol

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Reaction Steps

The desired 6-chloro-2,2-dimethylchroman-7-ol was synthesized from 4-chlororesorcinol as follows. A mixture of 3,3-dimethylacrylic acid (7.0 g) and 4-chlororesorcinol (10 g) in Eaton's reagent (50 mL) was stirred at ambient temperature for 16 h. At the end, the mixture was poured over ice and the precipitate was filtered, dried and crystallized from aqueous methanol to provide 6-chloro-7-hydroxy-2,2-dimethyl-2,3-dihydro-4H-chomen-4-one (8.7 g).

Provenance & Evidence