Hydrochloric Acid → Methyl [o-(5-hydroxy-2-nitrophenoxy)phenoxy]acetate

HRID 21514Notes

Reaction equation

HRID 21514 reaction equation
Cl.COC[O:5][C:6]1[CH:7]=[CH:8][C:9]([N+:25]([O-:27])=[O:26])=[C:10]([CH:24]=1)[O:11][C:12]1[CH:23]=[CH:22][CH:21]=[CH:20][C:13]=1[O:14][CH2:15][C:16]([O:18][CH3:19])=[O:17]>CO>[OH:5][C:6]1[CH:7]=[CH:8][C:9]([N+:25]([O-:27])=[O:26])=[C:10]([CH:24]=1)[O:11][C:12]1[CH:23]=[CH:22][CH:21]=[CH:20][C:13]=1[O:14][CH2:15][C:16]([O:18][CH3:19])=[O:17]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54326397Methyl {o-[5-(methoxymethoxy)-2-nitrophenoxy]phenoxy}acetate

Product 1

HCID 54060386Methyl [o-(5-hydroxy-2-nitrophenoxy)phenoxy]acetateYield 64.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.5N Hydrochloric acid (30 mL) is added to a solution of methyl {o-[5-(methoxymethoxy)-2-nitrophenoxy]phenoxy}acetate (3.35 g, 9.2 mmol) in methanol. The reaction mixture is refluxed for one hour, cooled to room temperature and concentrated in vacuo to give a residue. A solution of the residue in methylene chloride is washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to obtain the title product as a yellow liquid (1.9 g) which is identified by 1HNMR and 13CNMR spectral analyses.

Workup

  1. temperatureThe reaction mixture is refluxed for one hour
  2. concentrationconcentrated in vacuo
  3. customto give a residue
  4. washA solution of the residue in methylene chloride is washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-73876840c5ee449c9df53dbb2c0d575f
Source dataset
uspto-grants-1995_06
Patent number
US05424280

Reaction notes

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