Nitric Acid → Methyl 2-hydroxy-3-nitrobenzoate

HRID 1470612Notes

Reaction equation

HRID 1470612 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[N+:12]([O-])([OH:14])=[O:13]>C(O)(=O)C>[OH:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 4133Methyl Salicylate

Product 1

HCID 596904Methyl 2-hydroxy-3-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a ice cold solution of salicylic acid (10 g, 0.072 mol) in methanol (100 mL), was added drop wise SOCl2 (12.8 g, 0.1 mol). After the addition, the mixture was warmed to room temperature and heated to reflux for 12 h. After reaction is completed the reaction mixture was cooled to room temperature and the excess methanol was evaporated under reduced pressure to obtain 9 g of methyl 2-hydroxybenzoate as a white solid. (81%). A solution of methyl 2-hydroxybenzoate (9 g, 0.059 mol) in glacial acetic acid (90 mL) was cooled to 15° C., fuming nitric acid (11.2 mL) was added drop wise. The reaction mixture was warmed to room temperature and stirred for 4 h. When the reaction is completed, the reaction mixture was poured into crushed ice. The precipitate was collected by filtration and washed several times with chilled water, then dried in a vacuum oven to the required product as a yellow coloured solid.

Workup

  1. additionthe reaction mixture was poured
  2. custominto crushed ice
  3. filtrationThe precipitate was collected by filtration
  4. washwashed several times with chilled water
  5. dry with materialdried in a vacuum oven to the required product as a yellow coloured solid

Sources & evidence

ORD record
ord-f531786b7ea84c83adcab61cf61559ce
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

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