Water → HCID 13127031, compound

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen gas stream, resorcinol (55 g, 0.5 mol), potassium carbonate (207 g, 1.5 mol), water (25 ml, 1.4 mol) and N,N-dimethylformaldehyde (500 ml) were charged to a four necked flask (2 L) sufficiently dried, substituted with nitrogen, and equipped with a dropping funnel, Dimroth condenser tube, thermometer and stirring blade, so as to prepare a dimethylformaldehyde solution. Next, bromocylcohexane (408 g, 2.5 mol) was dropped through the dropping funnel for 10 minutes at room temperature, then this solution was heated at 80° C. for 14 hours by a mantle heater while stirring, and then heated at 100° C. for 11 hours. After the reaction terminated, it was stood to cool, and after it reached room temperature, it was cooled in an ice bath. The reaction solution was dissolved in 1 L toluene, and washed three times with 500 ml water. Toluen was distilled away by evaporation, and the residue was purified by column chromatography using hexane and ethyl acetate as developing solvents, to obtain a red brown objective product (hereinafter, referred to as R-1A) (21.9 g, 23% yield, 100% GC purity). The chemical shift value (δ ppm, TMS standard) of 1H-NMR of this compound in a heavy dimethyl sulfoxide solvent was 1.1 to 2.0 (m, 10H), 4.2 (m, H), 6.3 (m, 3H), 7.0 (m, H), 9.3 (s, H).

Provenance & Evidence