Acetone → HCID 10686529, compound

HRID 1395650Notes

Reaction equation

HRID 1395650 reaction equation
Br[CH:2]([CH2:8]Br)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[OH:10][C:11]1[CH:12]=[C:13]([CH:22]=[CH:23][C:24]=1[OH:25])[C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:15].C(=O)([O-])[O-].[K+].[K+].CC(C)=O>C(O)C>[C:14]([C:13]1[CH:22]=[CH:23][C:24]2[O:25][CH2:8][CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[O:10][C:11]=2[CH:12]=1)(=[O:15])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 97945Ethyl 2,3-dibromopropionateHCID 165870Methanone, (3,4-dihydroxyphenyl)phenyl-

Product 1

HCID 10686529HCID 10686529, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

11.63 ml of ethyl 2,3-dibromopropionate was added drop-by-drop over a 15-minute period to a mixture of 15.9 g of 5B, 58.5 g of anhydrous potassium carbonate and 250 ml of acetone. The stirred mixture was refluxed for 7 hours and stored overnight. The mixture was filtered and the solvent was evaporated from the filtrate under reduced pressure (40° C.). The residue was suspended in 600 ml of ether and the mixture was washed with water, then with sodium bicarbonate solution, then dried (MgSO4). The solvent was evaporated under reduced pressure. The residue was chromatographed over silica gel using chloroform as eluent. Workup with ether and removal of the solvent gave a residue which was suspended in ethanol and placed in a freezer overnight. The solid was collected, washed with ethanol and dried to give 5, mp: 70°-71° C.

Workup

  1. temperatureThe stirred mixture was refluxed for 7 hours
  2. filtrationThe mixture was filtered
  3. customthe solvent was evaporated from the filtrate under reduced pressure (40° C.)
  4. washthe mixture was washed with water
  5. dry with materialwith sodium bicarbonate solution, then dried (MgSO4)
  6. customThe solvent was evaporated under reduced pressure
  7. customThe residue was chromatographed over silica gel
  8. customWorkup with ether and removal of the solvent
  9. customgave a residue which
  10. waitplaced in a freezer overnight
  11. customThe solid was collected
  12. washwashed with ethanol
  13. customdried
  14. customto give 5, mp: 70°-71° C.

Sources & evidence

ORD record
ord-732a81b9389e46a8bfce5b50cd05ec2d
Source dataset
uspto-grants-1980_05
Patent number
US04205076

Reaction notes

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