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

HRID 638729Notes

Reaction equation

HRID 638729 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-nitrophenoxy)acetate 31 (100 g, 474 mmol) and concentrated HCl (1000 ml) was refluxed for 8 hours. The reaction mass was cooled to room temp. Crude 40 was filtered, dried and recrystallised from a mixture of ethyl acetate:hexane (1:5) to give pure 40 (86 g, 92.1%) as a white shining powder. M.p: 186-188.5° C.

Workup

  1. temperaturewas refluxed for 8 hours
  2. filtrationCrude 40 was filtered
  3. customdried
  4. customrecrystallised from a mixture of ethyl acetate:hexane (1:5)

Sources & evidence

ORD record
ord-1c9130ad281e4002980693fd0c6cf682
Source dataset
uspto-grants-2010_04
Patent number
US07691364B2

Reaction notes

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