Sulfuric Acid → HCID 19822234, compound

HRID 1030411Notes

Reaction equation

HRID 1030411 reaction equation
S(=O)(=O)(O)O.COC[O:9][C:10]1[C:11]([CH3:34])=[C:12]2[C:17](=[C:18]([CH3:21])[C:19]=1[CH3:20])[O:16][C:15]([CH3:33])([CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][N:25]=1)[CH2:14][CH2:13]2.C(=O)(O)[O-].[Na+]>C(O)(=O)C>[OH:9][C:10]1[C:11]([CH3:34])=[C:12]2[C:17](=[C:18]([CH3:21])[C:19]=1[CH3:20])[O:16][C:15]([CH3:33])([CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][N:25]=1)[CH2:14][CH2:13]2

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 19822168HCID 19822168, compound

Product 1

HCID 19822234HCID 19822234, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1 g of 10% w/v aqueous sulfuric acid was added to 45 ml of acetic acid containing 5.2 g of 6-methoxymethoxy-2,5,7,8-tetramethyl-2-(5-nitropyridin-2-yloxymethyl)chroman prepared as described in Preparation 34), and the resulting mixture was heated at 55°-58° C. for 15 minutes. The reaction mixture was cooled, poured into a mixture of 75 g of sodium bicarbonate and 75 g of ice, and then extracted with ethyl acetate. The extract was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue gave the title compound as a light-brown oil.

Workup

  1. customprepared
  2. customas described in Preparation 34), and the resulting mixture
  3. temperaturewas heated at 55°-58° C. for 15 minutes
  4. temperatureThe reaction mixture was cooled
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-1be297bd079040dfad8e20625a8aae53
Source dataset
uspto-grants-1992_04
Patent number
US05104888

Reaction notes

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