Sulfuric Acid → 4-Nitro-3-hydroxycinnamic acid

HRID 1956675Notes

Reaction equation

HRID 1956675 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[CH:5]=[CH:6][C:7]([OH:9])=[O:8].[N+:13]([O-])([O-:15])=[O:14].[Na+].S(=O)(=O)(O)O.N([O-])=O.[Na+]>C(Cl)Cl>[N+:13]([C:12]1[CH:11]=[CH:10][C:4]([CH:5]=[CH:6][C:7]([OH:9])=[O:8])=[CH:3][C:2]=1[OH:1])([O-:15])=[O:14]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 114963-(3-Hydroxyphenyl)-2-propenoic acidHCID 24268Sodium NitrateHCID 23668193Sodium Nitrite

Product 1

HCID 534017114-Nitro-3-hydroxycinnamic acidYield 26.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Hydroxycinnamic acid (3.00 g, 18.3 mmol) was dissolved in methylene chloride(40 mL) followed by the addition of sodium nitrate (1.70 g, 26.1 mmol). The addition of sulfuric acid (25 mL/3M) was then made, followed by addition of a catalytic amount of sodium nitrite. The mixture was allowed to stir. After 24 hours, the reaction mixture was diluted with methylene chloride and extracted with water. The organic layer was dried over MgSO4 and filtered. The solvent was evaporated and chromatography of the resulting solid on silica gel (4%MeOH/CH2Cl2) gave the desired product(1.0 g, 26%). 1H NMR (CD3COCD3): d 8.07 (d, 1H), 7.69 (d, 1H), 7.51 (s, 1H), 7.46 (d, 2H), 6.75 (d,1H).

Workup

  1. extractionextracted with water
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-5fdd5bde70c24a5ba5b26d67c13320cc
Source dataset
uspto-grants-1998_07
Patent number
US05780483

Reaction notes

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