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 Production Method of Methyl n-(p-methoxyphenyl)carbamate
  • Production Method of Methyl n-(p-methoxyphenyl)carbamate
  • Methyl n-(p-methoxyphenyl)carbamate (CAS NO.: ), with other names as , (4-methoxyphenyl)-, , could be produced through the following synthetic routes.

    Production Method of Methyl n-(p-methoxyphenyl)carbamate

    To a 1-L, round-bottomed flask equipped with a stirring bar are added p-methoxybenzamide (10 g, 66 mmol), N- (NBS) (11.9 g, 66 mmol), 1,8-diazabicyclo[5.4.0]undec-7-ene () (22 mL, 150 mmol) and (300 mL). The solution is heated at reflux for 15 min, at which point an additional aliquot of NBS (11.9 g, 66 mmol) is added slowly. The reaction is allowed to continue for another 30 min. Methanol is removed by rotary evaporation and the residue is dissolved in 500 mL of ethyl acetate (EtOAc). The EtOAc solution is washed with 6 N hydrochloric acid (HCl) (2 × 100 mL), 1 N sodium hydroxide (NaOH) (2 × 100 mL) and saturated sodium chloride (NaCl), and then dried over magnesium sulfate (MgSO4). The solvent is removed by rotary evaporation and the product, methyl N-(p-methoxyphenyl)carbamate, is purified by flash column chromatography [ 50 g of silica gel, EtOAc / hexane (1:1)] to give a pale yellow solid (11.1 g, 93%), which is further purified by recrystallization from 500 mL of hexane. Another 1.4 g of product (total 8.8 g, 73%) is obtained from the mother liquor by recrystallization from 100 mL of hexane .


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