Ethanol → 2-(4-CHLOROPHENYL)CHROMAN-4-ONE

HRID 1462949Notes

Reaction equation

HRID 1462949 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[OH:18])=[O:11])=[CH:4][CH:3]=1.C(O)C.C([O-])(=O)C.[Na+]>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:9][C:10](=[O:11])[C:12]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[O:18]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 344529HCID 344529, compoundHCID 517045Sodium Acetate

Product 1

HCID 2420652-(4-CHLOROPHENYL)CHROMAN-4-ONEYield 29%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

4-Chloro-2'-hydroxychalcone (5.17 g) was boiled under reflux with a mixture of ethanol (250 ml.) and a solution or sodium acetate (anhydrous, 4.10 g) in water (25 ml.) for 5 hrs. The reaction mixture was diluted with water and allowed to stand overnight. The solid precipitate was filtered off, washed with water and dried. Recrystallisation from petroleum ether (b.p. 80°-100° C.) gave 4'-chloroflavanone (1.50 g.), m.p. 96°-98° C.

Workup

  1. filtrationThe solid precipitate was filtered off
  2. washwashed with water
  3. customdried
  4. customRecrystallisation from petroleum ether (b.p. 80°-100° C.)

Sources & evidence

ORD record
ord-ebd8ec50ea9846bf862193f2374a75ad
Source dataset
uspto-grants-1984_07
Patent number
US04461907

Reaction notes

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