Hydrochloric Acid → HCID 14842375, compound

HRID 2231891Notes

Reaction equation

HRID 2231891 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].[C:12]([O:19][CH2:20][CH3:21])(=[O:18])[CH2:13][CH2:14][C:15]([CH3:17])=O.N1CCCC1.Cl>CCOCC.O.C1(C)C=CC=CC=1>[CH2:20]([O:19][C:12](=[O:18])[CH2:13][CH2:14][C:15]1([CH3:17])[CH2:10][C:9](=[O:11])[C:3]2[CH:4]=[CH:5][C:6]([OH:8])=[CH:7][C:2]=2[O:1]1)[CH3:21]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 69902',4'-DihydroxyacetophenoneHCID 10883Ethyl levulinateHCID 31268Pyrrolidine

Product 1

HCID 14842375HCID 14842375, compoundYield 58.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 30.4 g of 2',4'-dihydroxyacetophenone, 28.8 g of ethyl levulinate, 21.3 g of pyrrolidine, and 400 ml of toluene was stirred and refluxed for 3 hours with removal of water by means of a Dean-Stark trap. The resulting mixture was cooled in an ice bath and treated with 300 ml of 1.2N aqueous hydrochloric acid. After being stirred at room temperature for 45 minutes, the mixture was treated with ether and the aqueous layer was separated. The organic solution was washed with 1.2N hydrochloric acid. The aqueous acidic solutions were combined and extracted twice with ether. The organic solutions were combined, washed with water, saturated aqueous sodium bicarbonate and brine, then dried (magnesium sulfate), filtered and concentrated under reduced pressure. The residual red oil (42 g) was chromatographed on 400 g of silica gel. Elution with 9:1 toluene-ethyl acetate gave 32.3 g (58.1%) of racemic-3,4-dihydro-7-hydroxy-2-methyl-4-oxo-2H-1-benzopyran-2-propanoic acid ethyl ester as an orange, viscous oil.

Workup

  1. temperatureThe resulting mixture was cooled in an ice bath
  2. stirringAfter being stirred at room temperature for 45 minutes
  3. customthe aqueous layer was separated
  4. washThe organic solution was washed with 1.2N hydrochloric acid
  5. extractionextracted twice with ether
  6. washwashed with water, saturated aqueous sodium bicarbonate and brine
  7. dry with materialdried (magnesium sulfate)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residual red oil (42 g) was chromatographed on 400 g of silica gel
  11. washElution with 9:1 toluene-ethyl acetate

Sources & evidence

ORD record
ord-f12854a059e74d3a8582ccabded2e8e7
Source dataset
uspto-grants-1988_11
Patent number
US04785017

Reaction notes

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