Sodium Nitrate → Methyl 3-methyl-5-nitrosalicylate

HRID 909300Notes

Reaction equation

HRID 909300 reaction equation
[OH:1][C:2]1[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[N+:13]([O-])([O-:15])=[O:14].[Na+]>FC(F)(F)C(O)=O>[OH:1][C:2]1[C:11]([CH3:12])=[CH:10][C:9]([N+:13]([O-:15])=[O:14])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 24268Sodium NitrateHCID 31835Benzoic acid, 2-hydroxy-3-methyl-, methyl ester

Product 1

HCID 12099450Methyl 3-methyl-5-nitrosalicylateYield 64%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 2-hydroxy-3-methylbenzoate (Reference Compound No. 1-4-(1), 22.9 g, 0.138 mol) was dissolved in trifluoroacetic acid (190 mL), then an aqueous solution (90 mL) of sodium nitrate (12.9 g, 152 mmol) was added dropwise thereto over 1 hour at −10° C. After the reaction mixture was stirred at 0° C. for 1.5 hours, it was poured into ice-water (600 mL). The appeared solid was filtered and washed with methanol (100 mL) to give the titled reference compound (18.7 g) as a pale red solid. (Yield 64%)

Workup

  1. filtrationThe appeared solid was filtered
  2. washwashed with methanol (100 mL)

Sources & evidence

ORD record
ord-fb5093df25b94b91bb9453f46b22137c
Source dataset
uspto-grants-2011_09
Patent number
US08017775B2

Reaction notes

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