Methyl (4-nitrophenoxy)acetate → (4-Nitrophenoxy)acetic acid

HRID 1882327Notes

Reaction equation

HRID 1882327 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]([O:8][CH2:9][C:10]([O:12]C)=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]>Cl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:14][CH:15]=1)([O-:3])=[O:2]

Participants

3

Reactant 1

HCID 700522Methyl (4-nitrophenoxy)acetate

Product 1

HCID 15720(4-Nitrophenoxy)acetic acidYield 92.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of methyl (4-Nitro phenoxy)acetate 93 (100 grams, 474 mmol) and concentrated HCl (1000 mL) was refluxed for 8 hours. The reaction mass was cooled to room temperature. Crude 94 was filtered, dried, and recrystallized from a mixture of Ethyl acetate:Hexane (1:5) to give pure 94 (86 grams, 92.1%) as a white shining powder. M.p: 186-188.5° C.

Workup

  1. temperaturewas refluxed for 8 hours
  2. filtrationCrude 94 was filtered
  3. customdried
  4. customrecrystallized from a mixture of Ethyl acetate:Hexane (1:5)

Sources & evidence

ORD record
ord-b8be0723f9e24bd0b4c5c36995552ea8
Source dataset
uspto-grants-2012_11
Patent number
US08318973B2

Reaction notes

Loading…