Hydrochloric Acid → 6-(4-Amino-phenoxy)hexanoic acid hydrochloride

HRID 2169706Notes

Reaction equation

HRID 2169706 reaction equation
C[O:2][C:3](=[O:20])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16]C(=O)C)=[CH:12][CH:11]=1.[ClH:21]>>[ClH:21].[NH2:16][C:13]1[CH:12]=[CH:11][C:10]([O:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:20])=[O:2])=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 497644916-(4-Acetylaminophenoxy)-hexanoic acid methyl ester

Product 1

HCID 668113476-(4-Amino-phenoxy)hexanoic acid hydrochlorideYield 55.6%

Conditions

Temperature
10 °C

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.

Workup

  1. temperaturewas refluxed for 48 hours
  2. distillationExcess concentrated hydrochloric acid was distilled off in vacuum
  3. filtrationfiltered hot
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-7dd5648f0a1340bb865a9badd013dae3
Source dataset
uspto-grants-2015_06
Patent number
USRE045548E1

Reaction notes

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