Water → HCID 18475290, compound

HRID 2256273Notes

Reaction equation

HRID 2256273 reaction equation
C(OC(=O)C[C:6]([CH2:8][CH:9]([CH2:18][C:19](=[O:26])CC(OCC)=O)[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=1)=[O:7])C.[OH-:28].[Na+].[OH2:30]>C(O)C>[Cl:17][C:12]1[CH:11]=[C:10]([CH:9]([CH2:8][C:6]([OH:7])=[O:30])[CH2:18][C:19]([OH:26])=[O:28])[CH:15]=[CH:14][C:13]=1[Cl:16]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 131720106Diethyl-3,4-dichlorobenzal-bis-acetoacetate

Product 1

HCID 18475290HCID 18475290, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Diethyl-3,4-dichlorobenzal-bis-acetoacetate (155 g) in ethanol 2 L) was treated with 50% NaOH (2 L) and heated at reflux temperature for 4 hours. Water (1 L) was added to the reaction mixture and approx. 1.5 L of solvent removed by distillation. The remaining solution was poured onto ice (1 Kg) and sufficient HCl was added to adjust the pH to 1. The resulting solution was extracted with EtOAc (3×1.5 L) and the combined extracts dried over MgSO4, filtered and concentrated to give 100 g of the title compound.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 4 hours
  3. customremoved by distillation
  4. additionThe remaining solution was poured onto ice (1 Kg) and sufficient HCl
  5. additionwas added
  6. extractionThe resulting solution was extracted with EtOAc (3×1.5 L)
  7. dry with materialthe combined extracts dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-1aa13aa23092464d94969b0647202c6d
Source dataset
uspto-grants-1997_08
Patent number
US05654316

Reaction notes

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