Indene → HCID 131713525, compound

Participants

Reaction Steps

3-Chloro-2-hydroxybenzyl alcohol (20.0 g) (prepared by the method of Zincke, Hanus and Ziegler, J.Prakt. Chem., (2), 152 126(1939)), and indene (15 ml) were heated together at 190°-200° for 2.5 hr. The crude product was chromatographed on silica gel, eluting with toluene/60°-80° petroleum ether to yield a colourless oil (2.34 g) which was distilled in vacuo to give an oil which crystallised on standing (1.70 g., b.pt. 115°-120°/0.05 mmHg m.pt. 60°-63°). The recrystallised product, from ethanol was identified, by 1H-n.m.r., as cis-6-chloro-4b,10,10a,11-tetrahydrobenz(b)indeno(2,1-e) pyran, (1.20 g., m.pt-63°-65°).

Provenance & Evidence