Sulfuric Acid → 3-Nitro-2-hydroxycinnamic acid

HRID 612708

Reaction equation

HRID 612708 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[CH:4]=[CH:5][C:6]([OH:8])=[O:7].[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[C:2]([OH:1])=[C:3]([CH:9]=[CH:10][CH:11]=1)[CH:4]=[CH:5][C:6]([OH:8])=[O:7])([O-:15])=[O:14]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 119683-(2-Hydroxyphenyl)-2-propenoic acidHCID 24268Sodium NitrateHCID 23668193Sodium Nitrite

Product 1

HCID 534016493-Nitro-2-hydroxycinnamic acidYield 52.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-Hydroxycinnamic acid (3.00 g, 18.3 mmol) was dissolved in methylene chloride (40 mL) followed by the addition of sodium nitrate (2.21 g, 26.1 mmol). The addition of sulfuric acid (30 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 (2.0 g, 52%). 1H NMR (CD3COCD3): δ8.21 (d, 1H), 8.16 (d, 1H), 8.05 (d, 1H), 7.19 (t, 1H), 6.72 (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-53a2a58c9f704848b5f5087c7f3a766f
Source dataset
uspto-grants-1999_12
Patent number
US06005008

Linked notes

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