Reaction #2045039

ord-186d23c21cfc453899c658163c897378

Reaction equation

COC(=O)CCCCCOc1ccc([N+](=O)[O-])cc1
6-(4-nitrophenoxy) hexanoic acid methyl ester
COC(=O)CCCCCOc1ccc([N+](=O)[O-])cc1
6-(4-Nitro-phenoxy)-hexanoic acid methyl ester
O=C(O)CCCCCOc1ccc([N+](=O)[O-])cc1
53
Yield 80.2%
O=C(O)CCCCCOc1ccc([N+](=O)[O-])cc1
6-(4-Nitrophenoxy)-hexanoic acid
Yield 80.2%

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperaturewas refluxed for 16 hours
  2. 2
    Filtrationfiltered
  3. 3
    Otherdried
  4. 4
    Otherrecrystallised from a mixture of ethyl acetate:hexane (1:6)

Procedure

A mixture of 6-(4-nitrophenoxy) hexanoic acid methyl ester 39 (125 g, 468.16 mmol) and concentrated HCl (1250 ml) was refluxed for 16 hours. The reaction mixture was cooled to room temperature, filtered, dried and recrystallised from a mixture of ethyl acetate:hexane (1:6) to get pure 53 (95 g, 80.2%) as a white powder. M.p: 104-107° C.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08409559B2uspto-grants-2013_04