Methanol → Methyl 3-nitrobenzoate

HRID 1747191Notes

Reaction equation

HRID 1747191 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=[O:8])([O-:3])=[O:2].[N+](=[CH2:15])=[N-].CO>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([O:9][CH3:15])=[O:8])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 84973-Nitrobenzoic acidHCID 9550Diazomethane

Product 1

HCID 69260Methyl 3-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

3-Nitrobenzoic acid (1.00 g; 5.98 mmol; 1.00 eq.) is dissolved in toluene (15 ml). Timethylsilyl diazomethane in toluene and MeOH (1/1) (8.98 ml; 2.00 M; 17.95 mmol; 3.00 eq.) is added dropwise. The solution is stirred at RT for 1.5 h. Solvents are removed affording methyl 3-nitrobenzoate as a yellow powder (940.70 mg; 86.79%).

Workup

  1. customSolvents are removed

Sources & evidence

ORD record
ord-792ef25d6b844a059ecdd4a6b419937c
Source dataset
uspto-grants-2015_10
Patent number
US09150561B2

Reaction notes

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