Reaction #170973

Reaction equation

6-(4-Isocyanatophenoxy)-hexanoic acid methyl ester

ethylene glycol

→

19

Yield 84.0%

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

Yield 84.0%

Solvents

water

Conditions

Workup

1. 1
   Otherrose to 46° C
2. 2
   Filtrationafter which crude 19 was filtered
3. 3
   Otherdried
4. 4
   Otherrecrystallised from toluene

Procedure

6-(4-Isocyanatophenoxy)-hexanoic acid methyl ester 18 (15 g, 57 mmol) was added to ethylene glycol (50 ml) at room temp. The reaction was exothermic and the temp. rose to 46° C. Stirring at room temp. for 16 h. was followed by addition of water (150 ml), after which crude 19 was filtered, dried and recrystallised from toluene to get pure 19 (12 g, 84%) as a white powder with an m.p. between 69.5-71.5° C.

Source