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

HRID 1957829Notes

Reaction equation

HRID 1957829 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 668113476-(4-Amino-phenoxy)hexanoic acid hydrochloride

Product 1

HCID 146502966-(4-Aminophenoxy)-hexanoic acid methyl ester

Procedure

To a mixture of 6-(4-Amino-phenoxy)-hexanoic acid hydrochloride 20 (150 grams, 578 mmol) in methanol (3 liters) was passed dry HCl gas at 10° C. for 1 hour and refluxed for 48 hours. Methanol (1.5 liter) was distilled off, ice water (1 liter) was added and the pH was adjusted to 7.5 with K2CO3. Crude 21 was extracted into chloroform, washed with 5% NaHCO3 solution in water, dried over Na2SO4 and distilled to give 21 (60 g, 43.8) as a thick brown syrup. The structure was confirmed with NMR.

Workup

  1. customat 10° C.
  2. customfor 1 hour
  3. temperaturerefluxed for 48 hours
  4. distillationMethanol (1.5 liter) was distilled off
  5. additionice water (1 liter) was added
  6. extractionCrude 21 was extracted into chloroform
  7. washwashed with 5% NaHCO3 solution in water
  8. dry with materialdried over Na2SO4
  9. distillationdistilled

Sources & evidence

ORD record
ord-2f5fef9d77c2482bb3c3e908b6a3ff80
Source dataset
uspto-grants-2013_04
Patent number
US08409559B2

Reaction notes

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