Potassium Hydroxide → HCID 70021605, compound

HRID 411740Notes

Reaction equation

HRID 411740 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[CH:5]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]2[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:27])=[CH:14][CH:13]=1)[C:6]([O:8]CC)=[O:7])[CH3:2].[OH-].[K+]>C(O)C.O>[CH2:1]([O:3][C:4](=[O:28])[CH:5]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]2[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:27])=[CH:14][CH:13]=1)[C:6]([OH:8])=[O:7])[CH3:2]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 18541329HCID 18541329, compound

Product 1

HCID 70021605HCID 70021605, compoundYield 101.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of diethyl[4-(2,6-dichlorobenzyloxy)benzyl]malonate (3.02 g, 7.1 mmol) in ethanol (70 mL) with potassium hydroxide (0.48 g, 7.4 mmol) was stirred at room temperature for 18 h. The reaction mixture was diluted with water (100 mL) then concentrated to half the original volume in vacuo. The resulting aqueous solution was washed with ether then acidified with 3N HCl and the product extracted into ethyl acetate. The organic extract was washed with water then brine and dried (Na2SO4). Removal of solvent in vacuo afforded the title compound (2.86 g, 100%)

Workup

  1. concentrationthen concentrated to half the original volume in vacuo
  2. washThe resulting aqueous solution was washed with ether
  3. extractionthe product extracted into ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with water
  6. dry with materialbrine and dried (Na2SO4)
  7. customRemoval of solvent in vacuo

Sources & evidence

ORD record
ord-c82c39d4ddc04b96930c83b6e796c157
Source dataset
uspto-grants-2003_05
Patent number
US06559179B1

Reaction notes

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