Sulfuric Acid → HCID 86748211, compound

HRID 1708609Notes

Reaction equation

HRID 1708609 reaction equation
O[C:2]1[C:11]2[O:10][CH2:9][CH:8]([O:12][N+:13]([O-:15])=[O:14])[CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:16]([CH:18]1[O:20][CH2:19]1)Cl.[OH-].[Na+].S(=O)(=O)(O)[OH:24]>[Cl-].C[N+](C)(C)C.CO>[O:24]1[C:8]2([O:12][N+:13]([O-:15])=[O:14])[C:9]1([O:20][CH2:19][CH2:18][CH3:16])[O:10][C:11]1[CH:2]=[CH:3][CH:4]=[CH:5][C:6]=1[CH2:7]2

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 13210631HCID 13210631, compound

Product 1

HCID 86748211HCID 86748211, compoundYield 599.5%

Reagents, catalysts & solvents 2

HCID 6379Tetramethylammonium chlorideCatalystHCID 887MethanolSolvent2×

Procedure

3,4-Dihydro-8-hydroxy-3-nitroxy-2H-1-benzopyran (4.0 g) and 207 mg of tetramethylammonium chloride were added to 5.2 g of epichlorohydrin, and the mixture was stirred at room temperature for 48 hours. After the reaction, a solution of 1.2 g of sodium hydroxide in 60 ml of methanol was added at room temperature under stirring, and the mixture was stirred for 2 hours. A solution of 0.3 g of sulfuric acid in 4 ml of methanol was added to the reaction solution, and after stirring for 5 minutes the solvent was distilled away. The residue was extracted with chloroform and water added, and the chloroform layer was taken, washed with water and dried. Chloroform was distilled away, 30 ml of hexane was added to the residue, and the deposited matter was recovered by filtration, whereby 4.9 g of the desired product (yield 96.8%) was obtained as colorless crystalline powder.

Workup

  1. customAfter the reaction
  2. stirringunder stirring
  3. stirringthe mixture was stirred for 2 hours
  4. stirringafter stirring for 5 minutes the solvent
  5. distillationwas distilled away
  6. extractionThe residue was extracted with chloroform and water
  7. additionadded
  8. washwashed with water
  9. customdried
  10. distillationChloroform was distilled away
  11. addition30 ml of hexane was added to the residue
  12. filtrationthe deposited matter was recovered by filtration

Sources & evidence

ORD record
ord-b1e9b0c380b24f0889d213aae9e0e19b
Source dataset
uspto-grants-1994_10
Patent number
US05359097

Reaction notes

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