Tetrahydrofuran → HCID 22452679, compound

HRID 2185897Notes

Reaction equation

HRID 2185897 reaction equation
[O:1]([C:3]1[CH:4]=[C:5]([C:15]([O:17]C)=[O:16])[C:6]2[C:11]([C:12]=1[O:13][CH3:14])=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH3:2].C1COCC1.[OH-].[Na+]>O>[CH3:2][O:1][C:3]1[CH:4]=[C:5]([C:15]([OH:17])=[O:16])[C:6]2[C:11]([C:12]=1[O:13][CH3:14])=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 22452649HCID 22452649, compound

Product 1

HCID 22452679HCID 22452679, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of methyl 3,4-dimethoxyl-1-naphthalenecarboxylate (2.93 g, 11.9 mmol), THF (145 mL), water (58 mL), and 1N NaOH (25 mL, 25.0 mmol) was stirred at room temperature overnight. The THF was removed in vacuo and the mixture acidified to pH 1 with 1N HCl. The resulting white precipitate was extracted with EtOAc (2×50 mL), dried (MgSO4) and filtered to give the product as a white solid (2.55 g, 92%). 1H NMR (DMSO) δ 13.19 (s, 1H), 8.89 (d, 1H), 8.13 (d, 1H), 8.08 (s, 1H), 7.54 (m, 2H), 3.97 (s, 3H), 3.98 (s, 3H); MS (APCI) m/z 231 (M−H+).

Workup

  1. customThe THF was removed in vacuo
  2. extractionThe resulting white precipitate was extracted with EtOAc (2×50 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered

Sources & evidence

ORD record
ord-5b12fa14f1aa4627acf700a393e689ff
Source dataset
uspto-grants-2002_06
Patent number
US06403601B1

Reaction notes

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