Formaldehyde → HCID 13345181, compound

Participants

Reaction Steps

To a solution of 15 g of 2,7-di-t-butylthioxanthene in 150 mL of dry THF cooled to -75°, mL of n-butyl lithium solution (2.45 M) was added dropwise. A deep red color developed. After stirring at -75° for 30 min., 5 g of paraformaldehyde was added slowly. The mixture was then allowed to warm to room temperature and refluxed for 30 min. Completion of the reaction was signaled by discharge of the red color. The mixture, which contained a gray precipitate, was cooled and decomposed with ice and 25% H2SO4. Extraction of the aqueous layer with CH2Cl2, followed by washing of the extracts with H2O and saturated NaCl solution, drying over (MgSO4) and then evaporation gave an oily material which was purified by chromatography on silica gel by elution with hexane-ethyl acetate (95/5). The alcohol was obtained as a white solid, m.p. 158°-159°. Anal. calculated for C22H28OS: C, 77.64; H, 8.13; S, 9.41. Found: C, 77.72; H, 8.52; S, 9.28.

Provenance & Evidence