Sulfuric Acid → 4-Nitro-3-hydroxybenzophenone

HRID 1385416Notes

Reaction equation

HRID 1385416 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6].[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[CH:14]=[CH:13][C:4]([C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:6])=[CH:3][C:2]=1[OH:1])([O-:18])=[O:17]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 24268Sodium NitrateHCID 830503-HydroxybenzophenoneHCID 23668193Sodium Nitrite

Product 1

HCID 125631704-Nitro-3-hydroxybenzophenoneYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-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/CH2CH2) gave the desired product (1.10 g, 30%). 1H NMR (CD3COCD3): d 8.25 (d, 1H), 7.86 (d, 1H), 7.71 (m, 1H), 7.59 (d, 1H), 7.48 (s, 1H), 7.39 (dd, 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-03e6ceba4f4c414f8c3592116267ce08
Source dataset
uspto-grants-2001_07
Patent number
US06262113B1

Reaction notes

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