Nitric Acid → HCID 22397382, compound

HRID 1070666Notes

Reaction equation

HRID 1070666 reaction equation
[N+:1]([O-:4])(O)=[O:2].C(Cl)Cl.[OH:8][C:9]1[C:18]([OH:19])=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=1>C(OCC)C>[N+:1]([C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:17]=[C:18]([OH:19])[C:9]=1[OH:8])([O-:4])=[O:2]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 6344DichloromethaneHCID 70912,3-Dihydroxynaphthalene

Product 1

HCID 22397382HCID 22397382, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Fuming nitric acid (4.2 ml) was added to methylene chloride (50 ml) and the resulting solution diluted with diethyl ether (100 ml): Then 3-methylbuthylnitrite (1.9 ml) was added and this final solution added at 25-30° C. to a solution of 2,3-dihydroxynaphthalene (16.0 g) in ether (100 ml).The reaction mixture was washed with water, extracted into potassium bicarbonate (1 M), acidified and finally extracted into ether. After column chromatography (SiO2, toluene-ethyl acetate-acetic acid 18:1:1) the product was crystallized from toluene. Yield: 1.5 g, melting point 141-143° C.

Workup

  1. addition3-methylbuthylnitrite (1.9 ml) was added
  2. washwas washed with water
  3. extractionextracted into potassium bicarbonate (1 M)
  4. extractionfinally extracted into ether
  5. customAfter column chromatography (SiO2, toluene-ethyl acetate-acetic acid 18:1:1) the product was crystallized from toluene

Sources & evidence

ORD record
ord-7278cd7633b6437597d0b18877b88171
Source dataset
uspto-grants-2005_06
Patent number
US06903114B2

Reaction notes

Loading…