2'-Hydroxyacetophenone → 2-Methyl-2-(4-nitrophenoxymethyl)-4-oxochroman

HRID 2351511Notes

Reaction equation

HRID 2351511 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9].[N+:11]([C:14]1[CH:24]=[CH:23][C:17]([O:18][CH2:19][C:20](=O)[CH3:21])=[CH:16][CH:15]=1)([O-:13])=[O:12].N1CCCC1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.O>[CH3:21][C:20]1([CH2:19][O:18][C:17]2[CH:23]=[CH:24][C:14]([N+:11]([O-:13])=[O:12])=[CH:15][CH:16]=2)[CH2:9][C:8](=[O:10])[C:3]2[C:2](=[CH:7][CH:6]=[CH:5][CH:4]=2)[O:1]1

Participants

7

Reactant 4

HCID 83752'-HydroxyacetophenoneHCID 31268PyrrolidineHCID 3085071-(4-Nitrophenoxy)propan-2-oneHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 156139102-Methyl-2-(4-nitrophenoxymethyl)-4-oxochromanYield 54.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

2 g of o-hydroxyacetophenone, 2.85 g of 4-nitrophenoxyacetone, 2 g of pyrrolidine and 280 mg of p-toluenesufonic acid monohydrate were dissolved in 10 ml of toluene, and the mixture was heated under reflux for 3 hours in apparatus equipped with a water separator. At the end of this time, the reaction mixture was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was then distilled off under reduced pressure. The residue was subjected to silica gel column chromatography eluted with a 3:1 by volume mixture of benzene and ethyl acetate, to afford 2.5 g of the title compound as a pale yellow oily substance.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours in apparatus
  3. washAt the end of this time, the reaction mixture was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was then distilled off under reduced pressure
  6. washeluted with a 3:1 by volume mixture of benzene and ethyl acetate

Sources & evidence

ORD record
ord-c398bb4a97a04741b689d7d5447f9001
Source dataset
uspto-grants-1989_10
Patent number
US04873255

Reaction notes

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