Phosphorus oxychloride → [(4-Formylphenyl)azanediyl]di(hexane-6,1-diyl) diacetate

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Reaction Steps

N,N-Dimethylformamide (DMF, 250 mL) was added dropwise with stirring under nitrogen to phosphorous oxychloride (115 g, 0.751 mol) at 0° C. The resulting orange solution was stirred for 2 hours, then a solution of 236 g (0.626 mol) of N,N-di-(6-acetoxyhexyl)aniline (A2) in 250 mL of DMF was added slowly. The reaction mixture was stirred under nitrogen for 1 hour at 0° C. and then for 6 hours at 80° C. After cooling, the solution was poured onto 500 g of ice plus 200 g of sodium acetate, and the resulting mixture was extracted with dichloromethane (4×250 mL). The combined organic extracts were washed four times with 250 mL portions of water, dried over anhydrous sodium sulfate, and then concentrated at reduced pressure to produce a light brown oil. The oil was fractionally distilled in vacuo to yield 192 g (76%) of A3 as a gold oil, bp 220°-260° C. (0.007 mm).

Provenance & Evidence