2-(2-Methoxyphenoxy)benzoic acid → 2-(2-Hydroxyphenoxy)benzoic acid

HRID 982445Notes

Reaction equation

HRID 982445 reaction equation
C[O:2][C:3]1[CH:18]=[CH:17][CH:16]=[CH:15][C:4]=1[O:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=[O:9].Cl.N1C=CC=CC=1>O>[OH:2][C:3]1[CH:18]=[CH:17][CH:16]=[CH:15][C:4]=1[O:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=[O:9]

Participants

4

Reactant 2

HCID 5786892-(2-Methoxyphenoxy)benzoic acidHCID 10176127Pyridinium chloride

Product 1

HCID 6113882-(2-Hydroxyphenoxy)benzoic acidYield 48.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Fifteen grams of 2-(2-methoxyphenoxy)benzoic acid were heated at 180°-185° C. together with 150 g of pyridine hydrochloride for 3 hours. After cooling to room temperature, water was added and the mixture was stirred overnight at room temperature. The reaction was filtered and the water extracted several times with ethyl acetate. The combined ethyl acetate layers were dried and concentrated in vacuo. The crystallization of the residue from ethyl acetate/hexane provided 6.88 g of the desired subtitled intermediate, m.p. 147°-149° C.

Workup

  1. filtrationThe reaction was filtered
  2. dry with materialThe combined ethyl acetate layers were dried
  3. concentrationconcentrated in vacuo
  4. customThe crystallization of the residue from ethyl acetate/hexane

Sources & evidence

ORD record
ord-de504b9711f84cc39b90eaa286475094
Source dataset
uspto-grants-1991_02
Patent number
US04996230

Reaction notes

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