Nitric Acid → Benzoic acid, 4-hydroxy-3-nitro-, ethyl ester

HRID 866072Notes

Reaction equation

HRID 866072 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[N+:13]([O-])([OH:15])=[O:14]>C(O)(=O)C>[N+:13]([C:12]1[CH:11]=[C:5]([CH:4]=[CH:3][C:2]=1[OH:1])[C:6]([O:8][CH2:9][CH3:10])=[O:7])([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 8434Ethylparaben

Product 1

HCID 87895Benzoic acid, 4-hydroxy-3-nitro-, ethyl ester

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
40 °C

Procedure

To a stirred solution of 20.0 grams (0.12 mole) of ethyl 4-hydroxybenzoate in 200 mL of acetic acid was added a solution of 7.5 mL (excess) of 70% nitric acid in 30 mL of acetic acid. After the reaction mixture stirred for about one hour, it gradually turned orange and warmed to about 40° C. The reaction mixture was stirred for an additional eighteen hours and then was poured into 800 mL of ice-water. The mixture was stirred until the ice melted, and filtered to collect a solid, which was dissolved in ethyl acetate and dried with magnesium sulfate. The mixture was filtered, and the filtrate was concentrated under reduced pressure, yielding 22.0 grams of ethyl 3-nitro-4-hydroxybenzoate, mp 70°-71° C. The NMR spectrum was consistent with the proposed structure.

Workup

  1. stirringThe reaction mixture was stirred for an additional eighteen hours
  2. filtrationfiltered
  3. customto collect a solid, which
  4. dissolutionwas dissolved in ethyl acetate
  5. dry with materialdried with magnesium sulfate
  6. filtrationThe mixture was filtered
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3c28899a8a6e43a2b733190c7f054564
Source dataset
uspto-grants-1996_10
Patent number
US05569664

Reaction notes

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