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

HRID 2169724Notes

Reaction equation

HRID 2169724 reaction equation
C[O:2][C:3](=[O:15])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1>Cl>[N+:12]([C:9]1[CH:8]=[CH:7][C:6]([O:5][CH2:4][C:3]([OH:15])=[O:2])=[CH:11][CH:10]=1)([O-:14])=[O:13]

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-a74a17b3ea564bd7adba107583942128
Source dataset
uspto-grants-2015_06
Patent number
USRE045548E1

Reaction notes

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