Alkaline chlorination of the 4-alkyl-2,6-dichlorophenols (2b) and (2c) proceeds through ring contraction and halolactonization to form the 4α- alkyl-2,2,5α-trichloro-1α,3α-dihydroxycyclopentane-1,4-carbolactones (4b) and (4c). Under similar conditions, 2,4,6-trichlorophenol affords the analogous 2,2,4α,5α-tetrachloro-1α,3α-dihydroxycyclopentane-1,4- carbolactone (4a) in low yield, in addition to the Hantzsch acid (3a) as the major product. The acid (3a) upon further treatment undergoes chloro-lactonization to give the lactone (4a). The structures of the lactones (4b) and (4c) follow from spectroscopic comparison with (4a), the structure of which has been established by X-ray diffraction (C6H4Cl4O4 orthorhombic a 13.485(1), b 12.348(1), c 11.371(1) Ǻ, space group Pccn, Z 8, solved by direct methods and refined by block-diagonal and full-matrix least squares to R 0.031, Rw 0.043 for 1313 unique counter data with I/σ(I) ≥ 3.0).

Chaetomium globosum isolated from Cannabis sativa plant material converts (-)-Δ9-6a,10a-frans-tetrahydrocannabinol (Δ9-THC) (1a) into a number of metabolic products, which include the 3'-hydroxy, 11-hydroxy and 3',11-dihydroxy derivatives (1c), (1b) and (1d) respectively. The structure of the 3'-hydroxy-Δ9-THC (1c) has been confirmed by synthesis, whilst the structure of the 3',11-dihydroxy-Δ9-THC (1d) follows from mass spectroscopic comparison with the 3'-hydroxy and 11-hydroxy derivatives.

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Bei der alkalischen Chlorierung der Phenole (I) entstehen die Lactone (II).