Sulfuric Acid → HCID 21184664, compound

HRID 1385419Notes

Reaction equation

HRID 1385419 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:16]([O-])([O-:18])=[O:17].[Na+].S(=O)(=O)(O)O.N([O-])=O.[Na+]>C(Cl)Cl>[N+:16]([C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:10]=1[OH:15])([O-:18])=[O:17]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 24268Sodium NitrateHCID 804592-BenzyloxyphenolHCID 23668193Sodium Nitrite

Product 1

HCID 21184664HCID 21184664, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-Benzyloxyphenol (5.00 g, 25.0 mmol) was dissolved in methylene chloride (40 mL) followed by the addition of sodium nitrate (2.30 g, 27.5 mmol). The addition of sulfuric acid (3 l 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 (2.6 g, 43%). 1H NMR (CD3COCD3): d 7.70 (d, 1H), 7.50-7.28 (m, 5H), 7.14 (d, 1H), 6.92 (t, 1H), 5.21 (s, 2H).

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-678f45aba9d843bba9ce309e68a19031
Source dataset
uspto-grants-2001_07
Patent number
US06262113B1

Reaction notes

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