52956-20-4Relevant articles and documents
REARRANGEMENT OF 2-ACYL-2-CHLORO-1,3-CYCLOHEXANEDIONES INTO 2-ACYLRESORCINOLS AND 2-ACYL-4-CHLORO-1,3-CYCLOHEXANEDIONES
De Buyck, L.,Seynaeve, D.,De Kimpe, N.,Verhe, R.,Schamp, N.
, p. 363 - 370 (2007/10/02)
2-Acetylresorcinol was prepared in 80-88percent yield from 2-acetyl-1,3-cyclohexanedione by 2-chlorination (excess of NCS in boiling carbon tetrachloride or one equivalent of molecular chlorine in the cold solvent) followed by aromatization in a heated dry solution of hydrogen chloride in dimethylformamide.The scope of the method was extended to the preparation of 2-propionyl- and 2-isobutyrylresorcinol (resp. 79percent and 66percent yield).Application of the method on 2-acryl-5,5-dimethyl-1,3-cyclohexanediones (acyl=acetyl, propionyl, n-butyryl, i-butyryl) affrded the corresponding 2-acyl-4-chlorodimedone derivatives in 40-77percent yields.