Methanol → Salicylic acid, 4-nitro-, methyl ester

HRID 32284Notes

Reaction equation

HRID 32284 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].CO.[C:16]1(C)C=CC=CC=1.C[Si](C=[N+]=[N-])(C)C>CCCCCC>[CH3:16][O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][C:9]([N+:11]([O-:13])=[O:12])=[CH:10][C:2]=1[OH:1]

Participants

6

Reactant 4

HCID 887MethanolHCID 1140TolueneHCID 692664-Nitrosalicylic acidHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 139539Salicylic acid, 4-nitro-, methyl esterYield 100%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

916 mg (5 mmol) of 2-hydroxy-4-nitro-benzoic acid is dissolved in a mixture that consists of 8 ml of methanol and 32 ml of toluene, and it is slowly mixed with a solution of trimethylsilyldiazomethane in hexane (2 molar). After the addition is completed, stirring is continued for 1.25 hours at room temperature. After the reaction mixture is concentrated by evaporation, 1 g (about 100% of theory) of 2-hydroxy-4-nitro-benzoic acid methyl ester is obtained.

Workup

  1. additionAfter the addition
  2. concentrationAfter the reaction mixture is concentrated by evaporation

Sources & evidence

ORD record
ord-f4482a156b1b490eac5d912bb108e093
Source dataset
uspto-grants-2008_09
Patent number
US07427390B2

Reaction notes

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