2'-Hydroxyacetophenone → HCID 20441917, compound

HRID 1633176Notes

Reaction equation

HRID 1633176 reaction equation
N1CCCC1.[OH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13](=[O:15])[CH3:14].[C:16]([OH:23])(=[O:22])[CH2:17][CH2:18][C:19]([CH3:21])=O>C1(C)C=CC=CC=1>[CH3:21][C:19]1([CH2:18][CH2:17][C:16]([OH:23])=[O:22])[CH2:14][C:13](=[O:15])[C:8]2[C:7](=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:6]1

Participants

5

Reactant 3

HCID 83752'-HydroxyacetophenoneHCID 11579Levulinic AcidHCID 31268Pyrrolidine

Product 1

HCID 20441917HCID 20441917, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

24 g of pyrrolidine are added carefully, at under 30°, to a solution of 41 g of o-hydroxyacetophenone, 25 g of levulinic acid and 100 ml of toluene. The mixture is left to stand for 3 days at 25° and the solution is extracted by shaking with 150 ml of concentrated sodium carbonate solution. The aqueous phase is acidified with 2N HCl and then extracted by shaking with ether. The ethereal solution is concentrated and distilled, 14 g (20% of the theoretical yield) of 2-methyl-2-β-carboxyethyl-chroman-4-one being obtained: boiling point: 230°/0.1 mm Hg.

Workup

  1. waitThe mixture is left
  2. extractionthe solution is extracted
  3. extractionextracted
  4. stirringby shaking with ether
  5. concentrationThe ethereal solution is concentrated
  6. distillationdistilled

Sources & evidence

ORD record
ord-d4a6471f367e426ca619ce4e4573af49
Source dataset
uspto-grants-1984_10
Patent number
US04479007

Reaction notes

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