Hexane → Benzoic acid, 3-methyl-2-nitro-, methyl ester

HRID 1875551Notes

Reaction equation

HRID 1875551 reaction equation
[CH3:1]CCCCC.C[Si](C=[N+]=[N-])(C)C.[N+:14]([C:17]1[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:18]=1[C:19]([OH:21])=[O:20])([O-:16])=[O:15]>CC(C)=O>[N+:14]([C:17]1[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:18]=1[C:19]([O:21][CH3:1])=[O:20])([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 8058HexaneHCID 215753-Methyl-2-nitrobenzoic acidHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 79621Benzoic acid, 3-methyl-2-nitro-, methyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2M hexane solution (4.5 mL) of trimethylsilyldiazomethane was added to the mixture of 2-Nitro-3-methylbenzoic acid (1.6 g) and acetone (15 mL) and stirred for 3 hours. After removing the solvent, the residue was diluted with ethyl acetate and washed with 1M sodium hydrate aqueous solution, water and saturated aqueous solution of sodium chloride respectively. Then the obtained substance was concentrated and dried to obtain methyl 2-nitro-3-methylbenzoate.

Workup

  1. customAfter removing the solvent
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed with 1M sodium hydrate aqueous solution, water and saturated aqueous solution of sodium chloride respectively
  4. concentrationThen the obtained substance was concentrated
  5. customdried

Sources & evidence

ORD record
ord-084329c6df0848a3ae5cb1a5f6ac15e8
Source dataset
uspto-grants-2012_11
Patent number
US08309561B2

Reaction notes

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