Reaction #170987

Reaction equation

HCl

6-(4-nitrophenoxy)-hexanoic acid

6-(4-Nitrophenoxy)-hexanoic acid

ethylene glycol

HCl

→

6-(4-Nitrophenoxy)-hexanoic acid 2-hydroxy-ethyl ester

Conditions

Workup

1. 1
   Otherfor one hour
2. 2
   OtherDuring HCl gas bubbling the temperature
3. 3
   Otherrose to 60° C
4. 4
   OtherThe crude reaction mass
5. 5
   workup.ADDITIONwas poured onto ice (1 kg)
6. 6
   Extractionextracted in to ethyl acetate
7. 7
   Washwashed with water (2×250 ml)
8. 8
   Dryingdried over sodium sulphate
9. 9
   workup.DISTILLATIONdistilled
10. 10
    Otherto get crude 36, which
11. 11
    Otherwas purified by column chromatography on silica gel
12. 12
    Otherto get pure 36 (46 g, 78.3) as a light yellow syrup

Procedure

Dry HCl gas was passed through a mixture of 6-(4-nitrophenoxy)-hexanoic acid 35 (50 g, 197.62 mmol) and ethylene glycol (200 ml) was passed dry HCl gas for one hour. During HCl gas bubbling the temperature rose to 60° C. The crude reaction mass was poured onto ice (1 kg), extracted in to ethyl acetate, washed with water (2×250 ml), dried over sodium sulphate and distilled to get crude 36, which was purified by column chromatography on silica gel using benzene as eluant to get pure 36 (46 g, 78.3) as a light yellow syrup.

Source