Reaction #2045005

Reaction equation

(4-Aminophenoxy)acetic acid HCl

(4-Amino-phenoxy)acetic acid HCl

HCl

methanol

→

15

Yield 58.5%

(4-Amino-phenoxy)-acetic acid methyl ester

Yield 58.5%

Conditions

Workup

1. 1
   Otherat 10° C.
2. 2
   Otherfor 1 hour
3. 3
   Temperaturerefluxed for 10 hours
4. 4
   workup.DISTILLATIONMethanol (3.5 liters) was distilled off
5. 5
   workup.ADDITIONice water (1 liter) was added
6. 6
   FiltrationCrude 15 was filtered
7. 7
   Otherdried
8. 8
   Otherrecrystallised from a mixture of chloroform:hexane (1:5)

Procedure

To a mixture of (4-Aminophenoxy)acetic acid HCl 14 (250 g, 1.228 mol), in methanol (5 L) was passed dry HCl gas at 10° C. for 1 hour and refluxed for 10 hours. Methanol (3.5 liters) was distilled off, ice water (1 liter) was added and the pH was adjusted to 7.5 with K2CO3. Crude 15 was filtered, dried and recrystallised from a mixture of chloroform:hexane (1:5) to give pure 15 (130 g, 58.5%) as a light brown powder. The melting point was found to be 65-66.8° C.

Source