Toluene → HCID 21460859, compound

HRID 1941302Notes

Reaction equation

HRID 1941302 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:5]=1[OH:11])=[O:3].[CH2:12]([C:14]([CH2:16][CH3:17])=O)[CH3:13].N1CCCC1.C1(C)C=CC=CC=1>O>[CH2:12]([C:14]1([CH2:16][CH3:17])[CH2:1][C:2](=[O:3])[C:4]2[C:5](=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=2)[O:11]1)[CH3:13]

Participants

6

Reactant 4

HCID 1140TolueneHCID 69902',4'-DihydroxyacetophenoneHCID 7288Ethyl ketoneHCID 31268Pyrrolidine

Product 1

HCID 21460859HCID 21460859, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.52 g (10.0 mmoles) of resacetophenone are dissolved in 1.20 g (14.0 mmoles) of diethyl ketone, then 1.42 g (20.0 mmoles) pyrrolidine [prepared according to the method of H. J. Kabbe in Synthesis, 886 (1978)] are added thereto. The reaction mixture is allowed to stand at room temperature for 24 hours, then 40 ml of toluene are added. The reaction mixture is boiled under reflux for 10 hours by using a water separator. Then it is cooled back, washed subsequently with 10% hydrochloric acid and water, thereafter it is dried and evaporated to obtain 1.41 g of 2,2-diethyl-7-hydroxy-4-chromanone in the form of a pale yellow viscous oil which crystallizes on standing.

Workup

  1. customKabbe in Synthesis, 886 (1978)]
  2. additionare added
  3. temperatureunder reflux for 10 hours
  4. temperatureThen it is cooled back
  5. washwashed subsequently with 10% hydrochloric acid and water
  6. customit is dried
  7. customevaporated

Sources & evidence

ORD record
ord-37fdc828b00b460b97ceb0432bea0cac
Source dataset
uspto-grants-1997_12
Patent number
US05703113

Reaction notes

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