Hydrochloric Acid → 6-(4-Nitrophenoxy)hexanoic acid

HRID 1398249Notes

Reaction equation

HRID 1398249 reaction equation
C[O:2][C:3](=[O:19])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1.Cl>>[N+: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:19])=[O:2])=[CH:15][CH:14]=1)([O-:18])=[O:17]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 146502956-(4-Nitrophenoxy)-hexanoic acid methyl ester

Product 1

HCID 223889056-(4-Nitrophenoxy)hexanoic acidYield 80.2%

Procedure

A mixture of 6-(4-nitrophenoxy)-hexanoic acid methyl ester (125 g) and concentrated hydrochloride acid (1.2 L) was refluxed for 16 hours. The reaction mixture cooled was to room temperature, filtered, dried and recrystallised from a mixture of ethyl acetate and hexane (1:6) to obtain pure 6-(4-nitrophenoxy)-hexanoic acid (95 g) as a white powder with a melting point of 104-107° C. The product was characterized by 1H NMR (CDCl3) δ 1.60 (m, 2H, CH2), 1.76 (m, 2H, CH2), 1.90 (m, 2H, CH2), 2.42 (t, 2H, CH2), 4.04 (t, 2H2, OCH2), 6.96 (d, 2H, Ar), 8.20 (d, 2H, Ar).

Workup

  1. temperaturewas refluxed for 16 hours
  2. temperatureThe reaction mixture cooled
  3. customwas to room temperature
  4. filtrationfiltered
  5. customdried
  6. customrecrystallised from a mixture of ethyl acetate and hexane (1:6)

Sources & evidence

ORD record
ord-2174d4f0e694413da40bd625ca071901
Source dataset
uspto-grants-2014_12
Patent number
US08901347B1

Reaction notes

Loading…