Acetic Acid → HCID 18541329, compound

HRID 411739Notes

Reaction equation

HRID 411739 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[C:5](=[CH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[C:23]([Cl:24])=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:25])=[CH:12][CH:11]=1)[C:6]([O-:8])=[O:7])[CH3:2].[BH4-].[Na+].[C:29](O)(=O)[CH3:30]>C(O)C>[CH2:1]([O:3][C:4](=[O:26])[CH:5]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[C:23]([Cl:24])=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:25])=[CH:12][CH:11]=1)[C:6]([O:8][CH2:29][CH3:30])=[O:7])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 131723875HCID 131723875, compound

Product 1

HCID 18541329HCID 18541329, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

T a stirred solution of ethyl[4-(2,6-dichlorobenzyloxy)benzylidene]malonate (8.35 g, 19,2 mmol) in ethanol at 0° C. under argon was added sodium borohydride in small portions. Upon completion of the addition, the reaction mixture was adjusted to pH 6 with acetic acid. The mixture was filtered, concentrated in vacuo then partitioned between ether and water. The organic extract was washed successively with 1N hydrochloric acid, saturated sodium bicarbonate solution, water, brine and dried (MgSO4). Removal of volatiles in vacuo afforded the title compound (7.47 g, 88%).

Workup

  1. additionUpon completion of the addition
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated in vacuo
  4. customthen partitioned between ether and water
  5. extractionThe organic extract
  6. washwas washed successively with 1N hydrochloric acid, saturated sodium bicarbonate solution, water, brine
  7. dry with materialdried (MgSO4)
  8. customRemoval of volatiles in vacuo

Sources & evidence

ORD record
ord-33182d327ec641b8ae5b29e1dd783a09
Source dataset
uspto-grants-2003_05
Patent number
US06559179B1

Reaction notes

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