Hydrochloric Acid → HCID 19601772, compound

Participants

Reaction Steps

In a 41 three-neck flask with a mechanical stirrer, a solution of 5-tert-butyl-N,N′-dimethoxy-N,N′-dimethylisophthalamide (O5.106; 254 g, 560 mmol) in THF (700 ml) was slowly added dropwise within 2 h to methylmagnesium bromide (3 M in Et2O, 1.49 1, 4.48 mol). The solution was cooled during the addition, such that the temperature was kept between −10° C. and +5° C. On completion of addition, the cooling was removed and the reaction solution was stirred at RT for 16 h. The reaction solution was then added slowly to a cooled mixture of HCl (1 M, 500 ml) and ice. During this hydrolysis, the pH was kept between 3 and 6 by the addition of concentrated HCl. On completion of addition, MtB ether (1 l ) was added. The phases were separated and the aqueous phase was extracted with MtB ether (1×500 ml). The combined organic phases were dried (MgSO4), and the solvent was removed under reduced pressure. The product was obtained as a colorless oil (123 g). LC-MS rt: 1.50 min [M+H]+: 219 (met. a)

Provenance & Evidence