p-Toluenesulfonic acid monohydrate → HCID 19822239, compound

HRID 1030426Notes

Reaction equation

HRID 1030426 reaction equation
C(O[CH:5]1[C:14]2[C:9](=[CH:10][C:11]([C:19]([CH3:22])([CH3:21])[CH3:20])=[C:12]([O:15][C:16](=[O:18])[CH3:17])[CH:13]=2)[O:8][C:7]([CH3:34])([CH2:23][O:24][C:25]2[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=2)[CH2:6]1)(=O)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[C:16]([O:15][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][C:11]=1[C:19]([CH3:22])([CH3:21])[CH3:20])[O:8][C:7]([CH3:34])([CH2:23][O:24][C:25]1[CH:26]=[CH:27][C:28]([N+:31]([O-:33])=[O:32])=[CH:29][CH:30]=1)[CH:6]=[CH:5]2)(=[O:18])[CH3:17]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 19822212HCID 19822212, compound

Product 1

HCID 19822239HCID 19822239, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 2.4 g of 4,6-diacetoxy-7-t-butyl-2-methyl-2-(4-nitrophenoxymethyl)chroman (prepared as described in Preparation 56), 0.1 g of p-toluenesulfonic acid monohydrate and 50 ml of benzene was heated under reflux for 1 hour. The reaction solution was cooled, washed with a saturated aqueous solution of sodium bicarbonate, and then with water, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, to give the title compound as a yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. temperatureThe reaction solution was cooled
  4. washwashed with a saturated aqueous solution of sodium bicarbonate
  5. dry with materialwith water, and dried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-dbfb998ad8764ab3a5255e1b0d2ca01f
Source dataset
uspto-grants-1992_04
Patent number
US05104888

Reaction notes

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