Preparation method of 2,2,2-triphenylacetophenone_Kain Industrial Additive

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