Reaction #2045025

Reaction equation

6-(4-Isocyanato-phenoxy)-hexanoic acid methyl ester

ethylene glycol

→

37

Yield 84.0%

6-[4-(2-Hydroxy-ethoxycarbonylamino)-phenoxy]-hexanoic acid methyl ester

Yield 84.0%

Solvents

Water

Conditions

Workup

1. 1
   Otherrose to 46° C
2. 2
   Filtrationcrude 37 was filtered
3. 3
   Otherdried
4. 4
   Otherrecrystallised from toluene

Procedure

6-(4-Isocyanato-phenoxy)-hexanoic acid methyl ester 36 (15 g, 57 mmol) was added to ethylene glycol (50 ml) at room temperature. The reaction was exothermic and the temperature rose to 46° C. The reaction mixture was allowed to cool to room temperature and later stirred at room temperature for 16 hours. Water (150 ml) was added and crude 37 was filtered, dried and recrystallised from toluene to get pure 37 (12 g, 84%) as a white powder. M.p: 69.5-71.5° C.

Source