Sulfuric Acid → 3-Nitro-2-hydroxybenzophenone

HRID 1419422Notes

Reaction equation

HRID 1419422 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[N+:16]([O-])([O-:18])=[O:17].[Na+].S(=O)(=O)(O)O.N([O-])=O.[Na+]>C(Cl)Cl>[N+:16]([C:15]1[C:2]([OH:1])=[C:3]([CH:12]=[CH:13][CH:14]=1)[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5])([O-:18])=[O:17]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 83482'-HydroxybenzophenoneHCID 24268Sodium NitrateHCID 23668193Sodium Nitrite

Product 1

HCID 107053733-Nitro-2-hydroxybenzophenoneYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-Hydroxybenzophenone (3.00 g, 15.1 mmol) was dissolved in methylene chloride(40 mL) followed by the addition of sodium nitrate (1.42 g, 16.7 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(1.60 g, 44%). 1H NMR (CD3COCD3): δ 8.30 (d, 1H), 7.86 (m, 3H), 7.71 (m, 1H), 7.78 (d, 1H), 7.56 (dd 2H), 7.24 (t, 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-5cb79c24d439478591ae1f9d5e658c13
Source dataset
uspto-grants-1999_03
Patent number
US05886044

Reaction notes

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