Dimethyl 4-hydroxyisophthalate → 2-Hydroxy-5-(methoxycarbonyl)benzoic acid

HRID 528993Notes

Reaction equation

HRID 528993 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[CH:12][C:11]([OH:14])=[C:6]([C:7]([O:9]C)=[O:8])[CH:5]=1>N1C=CC=CC=1>[OH:14][C:11]1[CH:12]=[CH:13][C:4]([C:3]([O:2][CH3:1])=[O:15])=[CH:5][C:6]=1[C:7]([OH:9])=[O:8]

Participants

3

Reactant 1

HCID 80087Dimethyl 4-hydroxyisophthalate

Product 1

HCID 127170602-Hydroxy-5-(methoxycarbonyl)benzoic acidYield 100%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of dimethyl-4-hydroxyisophthalate (10.0 g, 47.6 mmol) in pyridine (70 mL) was heated to reflux for 15 h. The reaction mixture was concentrated in vacuo and acidified with 1N HCl at 0° C. The resulting solid was collected by filtration, washed with water and dried in vacuo to provide the title compound (9.3 g, 100%) as a white solid. 1H NMR (DMSO-d6) δ 8.40 (d, J=2.0 Hz, 1H), 8.06 (dd, J=8.4, 2.0 Hz, 1H), 7.07 (d, J=8.4 Hz, 1H), 3.84 (s, 3H); MS(ESI−) m/z 195.2 (M−H)−.

Workup

  1. temperatureto reflux for 15 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customacidified with 1N HCl at 0° C
  4. filtrationThe resulting solid was collected by filtration
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-7145ff93439d4f829dde23737dfd7ee9
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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