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

HRID 1957828Notes

Reaction equation

HRID 1957828 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-85bd14b99fbc404f9f80ebedc96c78c6
Source dataset
uspto-grants-2013_04
Patent number
US08409559B2

Reaction notes

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