Water → HCID 18670812, compound

HRID 993432Notes

Reaction equation

HRID 993432 reaction equation
[C:1]1([CH:11]=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Cl:13]C(Cl)C(OC)=O.C[C:21](C)([O-:23])C.[K+].[OH2:26].[C:27]([OH:31])([CH3:30])(C)C>CCCCCC.C(OCC)(=O)C>[Cl:13][CH:11]([C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)[C:27](=[O:31])[C:30]([O:23][CH3:21])=[O:26]

Participants

7

Reactant 5

HCID 962WaterHCID 61951-NaphthaldehydeHCID 6386tert-ButanolHCID 8315Methyl dichloroacetateHCID 23665647Potassium tert-butoxide

Product 1

HCID 18670812HCID 18670812, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

7.80 g (49.9 mmol) of 1-naphthaldehyde and 7.15 g (49.9 mmol) of methyl dichloroacetate were dissolved in 100 ml of t-butanol, and 6.15 g (54.8 mmol) of potassium t-butoxide was added thereto at 0° C. The mixture was stirred at room temperature for 24 hours and then 50 ml of water was added to stop the reaction. The solvent was removed under reduced pressure and the residue was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, concentrated and subjected to silica gel column chromatography(eluent: n-hexane/ethyl acetate=90/10, v/v) to give 2.5 g (9.52 mmol, Yield 19%) of the title compound.

Workup

  1. customat 0° C
  2. customthe reaction
  3. customThe solvent was removed under reduced pressure
  4. extractionthe residue was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3ae4047df74d411c81d18a63aa150ca4
Source dataset
uspto-grants-2002_10
Patent number
US06472526B1

Reaction notes

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