Methyl Salicylate → Methyl 2-(3-methyl-4-nitrophenoxy)benzoate

HRID 1269850Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].F[C:8]1[CH:9]=[CH:10][C:11]([N+:15]([O-:17])=[O:16])=[C:12]([CH3:14])[CH:13]=1.[C:18]([O:27][CH3:28])(=[O:26])[C:19]1[C:20](=[CH:22][CH:23]=[CH:24][CH:25]=1)[OH:21].[Cl-].[Na+]>CN(C)C=O>[CH3:14][C:12]1[CH:13]=[C:8]([CH:9]=[CH:10][C:11]=1[N+:15]([O-:17])=[O:16])[O:21][C:20]1[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=1[C:18]([O:27][CH3:28])=[O:26]

Participants

Conditions

Temperature: 140 °C

Procedure

Potassium carbonate (1.16 g, 8.39 mmol) was added to a solution of 5-fluoro-2-nitrotoluene (1.0 g, 6.45 mmol) and methyl salicylate (1.18 g, 7.74 mmol) in N,N-dimethylformamide (8 ml), and the resulting mixture was stirred at 140° C. for 1 hour. After the reaction, the reaction solution was cooled to 0° C. and a saturated aqueous sodium chloride solution was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. The organic layer dried was concentrated and then purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=10/1) to obtain methyl 2-(3-methyl-4-nitrophenoxy)benzoate (1.88 g, 85%).

Workup

customAfter the reaction
temperaturethe reaction solution was cooled to 0° C.
extractionfollowed by extraction with ethyl acetate
washThe organic layer was washed with water
dry with materiala saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate
customThe organic layer dried
concentrationwas concentrated
custompurified by a silica gel column chromatography (eluent: hexane/ethyl acetate=10/1)

Sources & evidence

ORD record: ord-d929e9ee1e0f4492ae914718b34d0cef
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07199147B2

Reaction notes

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