Reaction #2045008

Reaction equation

2-(4-Amino-phenoxy)-propionic acid

HCl

methanol

→

18

Yield 37.2%

2-(4-Amino-phenoxy)-propionic acid methyl ester

Yield 37.2%

Conditions

Workup

1. 1
   Otherat 10° C.
2. 2
   Otherfor 1 hour
3. 3
   Temperaturerefluxed for 48 hours
4. 4
   workup.DISTILLATIONMethanol (2.5 liter) was distilled off
5. 5
   workup.ADDITIONice water (1 liter) was added
6. 6
   ExtractionCrude 18 was extracted into chloroform
7. 7
   Washwashed with 5% NaHCO3 solution, water
8. 8
   Dryingdried over Na2SO4
9. 9
   workup.DISTILLATIONdistilled

Procedure

To a mixture of 2-(4-Amino-phenoxy)-propionic acid 17 (240 g, 1.103 mol), in methanol (4.8 liters) was passed dry HCl gas at 10° C. for 1 hour and refluxed for 48 hours. Methanol (2.5 liter) was distilled off, ice water (1 liter) was added and the pH was adjusted to 7.5 with K2CO3. Crude 18 was extracted into chloroform, washed with 5% NaHCO3 solution, water, dried over Na2SO4 and distilled to give 18 (80 g, 37.2%) as a brown syrup. The structure was confirmed with NMR.

Source