background and overview[1]
2,2,2-triphenylacetophenone can be used as a pharmaceutical synthesis intermediate. if 2,2,2-triphenylacetophenone is inhaled, move the patient to fresh air; if skin contact occurs, take off contaminated clothing, rinse the skin thoroughly with soap and water, and seek medical attention if you feel unwell. ; if eye contact occurs, separate eyelids, rinse with running water or saline, and seek medical attention immediately; if ingested, rinse mouth immediately, do not induce vomiting, and seek medical attention immediately.
preparation[1]
preparation of phenyltriphenylmethylketone (2,2,2-triphenylacetophenone) by rearrangement of pinacol. sulfonimide is used as the reaction raw material. sulfonimide is non-toxic, non-volatile and non-corrosive. another valuable aspect is that it can be easily recovered from the reaction mixture in high yield, which has economic and ecological advantages. the specific steps are: add phthalomethanesulfonimide (1; 20 mol%; 0.066g, 0.3mmol) to 1,1,2,2-tetrakis-1,2-diol (0.55g, 1.5mmol) ) in toluene (10 ml), and the mixture was stirred at 110 °c for 7 h. the reaction was monitored by tlc, gc and gc-ms analysis until complete conversion to the desired product. pour the mixture into et2o-h2o (40 ml, 1:1), separate the aqueous layer, wash the organic extracts with h2o (20 ml), dry (na2so4), and evaporate under reduced pressure. the crude residue was purified by flash chromatography (pe-et2o, 9:1) to give pure 2,2,2-triphenylacetophenone. yield: 0.52g (100%); white solid. melting point 182.5-183.2℃ (toluene-pe) (lit. 41185-187℃). 1hnmr (200mhz, cdcl3): δ=7.09-7.24 (m, 18h), 7.59-7.63 (m, 2h). 13cnmr (50mhz, cdcl3): δ=71.2, 126.87 (3℃), 127.80 (2℃), 127.99 (6℃), 131.10 (6℃), 131.25 (2℃), 131.88, 137.66, 143.39 (3c), 199.03. ir(ccl4): 1684(co)cm-1.
main reference materials
[1] o-benzenedisulfonimide as reusable brønsted acid catalyst for acid-catalyzed organic reactions
