1-Butanol → 5-Butoxy-2-nitrobenzoic acid methyl ester

HRID 72197

Reaction equation

HRID 72197 reaction equation
[H-].[Na+].[CH2:3]([OH:7])[CH2:4][CH2:5][CH3:6].C(=O)=O.[CH3:11][O:12][C:13](=[O:24])[C:14]1[CH:19]=[C:18](F)[CH:17]=[CH:16][C:15]=1[N+:21]([O-:23])=[O:22]>CN(C=O)C.C(OCC)(=O)C>[CH3:11][O:12][C:13](=[O:24])[C:14]1[CH:19]=[C:18]([O:7][CH2:3][CH2:4][CH2:5][CH3:6])[CH:17]=[CH:16][C:15]=1[N+:21]([O-:23])=[O:22]

Participants

7

Reactant 4

HCID 2631-ButanolHCID 280Carbon DioxideHCID 24758Sodium hydrideHCID 51520495-Fluoro-2-nitrobenzoic acid methyl ester

Product 1

HCID 689764995-Butoxy-2-nitrobenzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (302.4 mg) was added to a solution of 1-butanol (0.634 mL) in DMF (15 mL). The reaction mixture was stirred until there was no further evolution of CO2 and then 5-fluoro-2-nitrobenzoic acid methyl ester (1.15 g) was added and the mixture was stirred at room temperature overnight. The reaction was then mixed with ethyl acetate, washed with 10% sodium bicarbonate and 10% citric acid solution, dried over sodium sulfate and concentrated. The crude product was purified by preparative HPLC. The product with the molecular weight of 253.26 (C12H15NO5) was obtained in this way; MS (ESI): 254 (M+H+).

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. washwashed with 10% sodium bicarbonate and 10% citric acid solution
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe crude product was purified by preparative HPLC
  6. customThe product with the molecular weight of 253.26 (C12H15NO5) was obtained in this way

Sources & evidence

ORD record
ord-bb61bd3967b346ddbd2607904150f60b
Source dataset
uspto-grants-2014_09
Patent number
US08828991B2

Linked notes

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