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

HRID 501839Notes

Reaction equation

HRID 501839 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

6-(4-acetylaminophenoxy)-hexanoic acid methyl ester 15 (290 g, 1.04 mol), in conc. HCl (7.12 L) was refluxed for 48 hours. Excess conc. HCl was distilled off in vacuum and filtered hot. The mixture was cooled to 10° C., filtered and dried to give pure 16 (150 g, 55.6%) as a brown powder with an m.p between 155-160° C.

Workup

  1. distillationExcess conc. HCl was distilled off in vacuum
  2. filtrationfiltered hot
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-d62a41bbcbce4fa7b93f72201f0aa43d
Source dataset
uspto-grants-2010_08
Patent number
US07772352B2

Reaction notes

Loading…