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

HRID 2405181Notes

Reaction equation

HRID 2405181 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 66 (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, ice water (1 liter) was added and the pH was adjusted to 7.5 with K2CO3. Crude 67 was extracted into chloroform, washed with 5% NaHCO3 solution, water, dried over Na2SO4 and distilled to give 67 (60 grams, 43.8) as a thick brown syrup. The structure was confirmed with NMR. IHNMR (CDCl3) δ 1.5 (m, 2H,CH2), 1.72(m, 4H, CH2), 2.34(t, 2H, CH2), 3.66(s,3H,ester), 3.85(t,2H,OCH2), 6.56(d,2H,Ar), 6.68(d,2H,Ar).

Workup

  1. customat 10° C.
  2. customfor 1 hour
  3. temperaturerefluxed for 48 hours
  4. distillationMethanol (1.5 liter) was distilled
  5. additionice water (1 liter) was added
  6. extractionCrude 67 was extracted into chloroform
  7. washwashed with 5% NaHCO3 solution, water
  8. dry with materialdried over Na2SO4
  9. distillationdistilled

Sources & evidence

ORD record
ord-ef64de3788614d1e89cfe930588939a3
Source dataset
uspto-grants-2014_08
Patent number
US08802892B2

Reaction notes

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