Ethyl Acetate → HCID 54535871, compound

HRID 486539Notes

Reaction equation

HRID 486539 reaction equation
[CH3:1][O:2][CH:3]([O:20][CH3:21])[CH2:4][CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Cl:15])[CH:11]=2)[C:6]1=NN(C)C.C(OCC)(=[O:24])C>O1CCCC1.P([O-])([O-])([O-])=O.O.O.[Cu](Cl)Cl>[CH3:1][O:2][CH:3]([O:20][CH3:21])[CH2:4][CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Cl:15])[CH:11]=2)[C:6]1=[O:24].[Cl:15][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[C:6](=[O:24])[CH:5]([CH2:4][CH:3]=[O:2])[CH2:14][CH2:13]2

Participants

7

Reactant 2

HCID 8857Ethyl AcetateHCID 67850248HCID 67850248, compound

Product 2

HCID 19095431HCID 19095431, compoundYield 24%HCID 54535871HCID 54535871, compoundYield 43%

Reagents, catalysts & solvents 3

HCID 61482Cupric chloride dihydrateCatalystHCID 1061PhosphateSolventHCID 8028TetrahydrofuranSolvent

Procedure

6-Chloro-1-(dimethylhydrazono)-1,2,3,4-tetrahydro-2-naphthaleneacetaldehyde dimethyl acetal (10.3 g) was dissolved under argon in a mixture of 500 ml of tetrahydrofuran and 265 ml of 0.067M phosphate buffer of pH value 7. The solution was treated with 8.7 g of copper(II) chloride dihydrate and stirred at room temperature for 18 hours. 400 ml of ethyl acetate were added to the reaction mixture and it was washed twice with 500 ml of a mixture of 25% ammonia solution and saturated ammonium chloride solution (1:19) each time. The aqueous wash phases were extracted three times with 200 ml of ethyl acetate each time, the organic phases were combined, dried over MgSO4 and freed from solvent. The crude product, 8.2 g of brown oil, was chromatographed on 330 g of silica gel with ethyl acetate/hexane mixtures (1:6 to 1:4) as the eluent. There were obtained 2.1 g (24%) of 6-chloro-1,2,3,4-tetrahydro-1-oxo-2-naphthaleneacetaldehyde dimethyl acetal besides 3.2 g (43%) of 6-chloro-1,2,3,4-tetrahydro-1-oxo-2-naphthaleneacetaldehyde.

Workup

  1. washwas washed twice with 500 ml of a mixture of 25% ammonia solution and saturated ammonium chloride solution (1:19) each time
  2. extractionThe aqueous wash phases were extracted three times with 200 ml of ethyl acetate each time
  3. dry with materialdried over MgSO4
  4. customThe crude product, 8.2 g of brown oil, was chromatographed on 330 g of silica gel with ethyl acetate/hexane

Sources & evidence

ORD record
ord-c4288d54415245749a8137196721cb6e
Source dataset
uspto-grants-1994_03
Patent number
US05292732

Reaction notes

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