Hydrochloric Acid → 6-(4-Aminophenoxy)-hexanoic acid methyl ester

HRID 83788

Reaction equation

HRID 83788 reaction equation
Cl.[NH2:2][C:3]1[CH:17]=[CH:16][C:6]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:5][CH:4]=1.Cl.[CH3:19]O>>[CH3:19][O:14][C:13](=[O:15])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][O:7][C:6]1[CH:5]=[CH:4][C:3]([NH2:2])=[CH:17][CH:16]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 66811347HCID 66811347, compound

Product 1

HCID 146502966-(4-Aminophenoxy)-hexanoic acid methyl esterYield 43.8%

Procedure

Method-A Through a mixture of 6-(4-aminophenoxy)-hexanoic acid hydrochloride 16 (150 g, 578 mmol) in methanol (3 L) was passed dry HCl gas at 10° C. for 1 hour and refluxed for 48 hours. Methanol (1.5 L) was distilled off, ice water (1 L) was added and the pH adjusted to 7.5 with K2CO3. Crude 17 was extracted into chloroform, washed with 5% NaHCO3 solution, then water, and then dried over Na2SO4 and distilled to give 17 (60 g, 43.8%) as a thick brown syrup. Method-B 6-(4-Nitrophenoxy)-hexanoic acid methyl ester 21 (40 g, 149.81 mmol) was dissolved in dimethyl formamide (200 ml) in a pressure vessel. Raney nickel (20 g) was added and the mixture stirred under an atmosphere of hydrogen (4 kg) for 16 hours. Catalyst was removed by filtration and dimethyl formamide distilled off under vacuum. Crude 17 was purified by column chromatography on silica gel using chloroform as eluant to get pure 17 (28 grams, 78.8%) as a thick brown syrup.

Workup

  1. customat 10° C.
  2. customfor 1 hour
  3. temperaturerefluxed for 48 hours
  4. distillationMethanol (1.5 L) was distilled off
  5. additionice water (1 L) was added
  6. extractionCrude 17 was extracted into chloroform
  7. washwashed with 5% NaHCO3 solution
  8. dry with materialwater, and then dried over Na2SO4
  9. distillationdistilled

Sources & evidence

ORD record
ord-53b650998968494ea4af0ab1be506de0
Source dataset
uspto-grants-2014_09
Patent number
US08846845B2

Linked notes

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