Reaction #2045040

Reaction equation

6-(4-nitrophenoxy)hexanoic acid

6-(4-Nitrophenoxy)-hexanoic acid

ethylene glycol

HCl

→

54

Yield 78.3%

6-(4-Nitrophenoxy)hexanoic acid 2-hydroxyethyl ester

Yield 78.3%

Conditions

Workup

1. 1
   Otherfor one hr
2. 2
   OtherDuring HCl gas bubbling the temp
3. 3
   Otherrose to 60° C
4. 4
   OtherThe crude reaction mass
5. 5
   workup.ADDITIONwas poured onto ice (1 Kg)
6. 6
   Extractionextracted into 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 54, which
11. 11
    Otherwas purified by column chromatography on silica gel

Procedure

To a mixture of 6-(4-nitrophenoxy)hexanoic acid 53 (50 g, 197.62 mmol) and ethylene glycol (200 ml) was passed dry HCl gas for one hr. During HCl gas bubbling the temp. rose to 60° C. The crude reaction mass was poured onto ice (1 Kg), extracted into ethyl acetate, washed with water (2×250 ml), dried over sodium sulphate and distilled to get crude 54, which was purified by column chromatography on silica gel using benzene as eluant to get pure 54 (46 g, 78.3%) as a light yellow syrup.

Source