2'-Hydroxyacetophenone → HCID 20441917, compound

HRID 1649262Notes

Reaction equation

HRID 1649262 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 2 N 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-80b38afc1e7a4c04867889e775f9c142
Source dataset
uspto-grants-1983_11
Patent number
US04415741

Reaction notes

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