Reaction #2045010

Reaction equation

6-(4-Acetylaminophenoxy)hexanoic acid methyl ester

6-(4-Acetylamino-phenoxy)-hexanoic acid methyl ester

hydrochloric acid

→

20

Yield 55.6%

6-(4-Amino-phenoxy)-hexanoic acid Hydrochloride

Yield 55.6%

Conditions

Workup

1. 1
   Temperaturewas refluxed for 48 hours
2. 2
   workup.DISTILLATIONExcess concentrated hydrochloric acid was distilled off in vacuum
3. 3
   Filtrationfiltered hot
4. 4
   Filtrationfiltered
5. 5
   Otherdried

Procedure

A mixture of 6-(4-Acetylaminophenoxy)hexanoic acid methyl ester 19 (290 grams, 1.04 mol) in concentrated hydrochloric acid (7.12 L) was refluxed for 48 hours. Excess concentrated hydrochloric acid was distilled off in vacuum and filtered hot. The mixture was cooled to 10° C., filtered and dried give pure 20 (150 g, 55.6%) as a brown powder. The melting point was found to be 155-160° C.

Source