Acetone → HCID 67723520, compound

HRID 1682546Notes

Reaction equation

HRID 1682546 reaction equation
C([O:3][C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:7]1)=[O:5])C.[OH-].[Na+].CC(C)=O.[ClH:29]>C(O)C.O>[ClH:29].[O:16]([CH2:15][CH2:14][CH2:13][CH2:12][N:8]1[CH2:9][CH2:10][CH2:11][C@@H:6]([C:4]([OH:5])=[O:3])[CH2:7]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 8054225HCID 8054225, compound

Product 1

HCID 67723520HCID 67723520, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The above ester (3.5 g, 11.5 mmol) was dissolved in ethanol (35 ml) and 4N sodium hydroxide (5.7 ml) was added. The mixture was stirred at ambient temperature overnight. The reaction mixture was diluted with water and 4M hydrochloric acid (11.5 ml) was added. The mixture was concentrated in vacuo and dichloromethane (50 ml) and acetone were added to the residue. The mixture was concentrated in vacuo to give a residue which was heated at reflux with acetone (700 ml). The mixture was filtered while still hot and the filtrate was left for crystallisation. The solid which formed was isolated by filtration and dried to give 1.9 g of the title compound as a solid.

Workup

  1. additionwas added
  2. concentrationThe mixture was concentrated in vacuo and dichloromethane (50 ml) and acetone
  3. additionwere added to the residue
  4. concentrationThe mixture was concentrated in vacuo
  5. customto give a residue which
  6. temperaturewas heated
  7. filtrationThe mixture was filtered while still hot and the filtrate
  8. waitwas left for crystallisation
  9. customThe solid which formed
  10. customwas isolated by filtration
  11. customdried

Sources & evidence

ORD record
ord-5ab48f1f2ae04927877406d44d9c3c85
Source dataset
uspto-grants-1997_06
Patent number
US05635518

Reaction notes

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