Water → HCID 86737101, compound

HRID 2057956Notes

Reaction equation

HRID 2057956 reaction equation
[CH2:1]([C:8]1[CH:15]=[C:12]([CH:13]=O)[C:11]([OH:16])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH:24](C(OCC)=O)[C:25]([O:27][CH2:28][CH3:29])=[O:26].O>CC(=O)CC>[CH2:1]([C:8]1[CH:9]=[CH:10][C:11]2[O:16][C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:13][C:12]=2[CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 69637Diethyl bromomalonateHCID 45126705-Benzyl-2-hydroxy-benzaldehyde

Product 1

HCID 86737101HCID 86737101, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

6.9 g of 1A was dissolved in 130 ml of 2-butanone. The solution was heated to reflux and 8.1 g of potassium carbonate was added. Then 7.8 g of diethyl bromomalonate was added, drop-by-drop over a 10-minute period. The mixture was stirred at reflux for 58 hours, then was cooled and filtered. The filtrate was concentrated under reduced pressure to leave an oil, which was poured into water. The mixture was extracted with ether. The extract was washed with 5% sodium hydroxide solution, then with water, dried (MgSO4), and concentrated under reduced pressure. The residue was recrystallized from methanol and dried over P2O5 to give 1, mp: 78°-79° C.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux
  3. temperatureat reflux for 58 hours
  4. temperaturewas cooled
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customto leave an oil, which
  8. extractionThe mixture was extracted with ether
  9. washThe extract was washed with 5% sodium hydroxide solution
  10. dry with materialwith water, dried (MgSO4)
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was recrystallized from methanol
  13. dry with materialdried over P2O5
  14. customto give 1, mp: 78°-79° C.

Sources & evidence

ORD record
ord-4f6353ca7a484d2a823b8c5cefdbecad
Source dataset
uspto-grants-1980_07
Patent number
US04213999

Reaction notes

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