Ethyl Acetate → HCID 19095295, compound

HRID 486589Notes

Reaction equation

HRID 486589 reaction equation
[CH3:1][O:2][CH:3]([O:21][CH3:22])[CH2:4][CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][C:9]([O:15][CH3:16])=[CH:10][CH:11]=2)[C:6]1=NN(C)C.C(OCC)(=[O:25])C>O1CCCC1.P([O-])([O-])([O-])=O.O.O.[Cu](Cl)Cl>[CH3:1][O:2][CH:3]([O:21][CH3:22])[CH2:4][CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][C:9]([O:15][CH3:16])=[CH:10][CH:11]=2)[C:6]1=[O:25]

Participants

6

Reactant 2

HCID 8857Ethyl AcetateHCID 67850216HCID 67850216, compound

Product 1

HCID 19095295HCID 19095295, compound

Reagents, catalysts & solvents 3

HCID 61482Cupric chloride dihydrateCatalystHCID 1061PhosphateSolventHCID 8028TetrahydrofuranSolvent

Procedure

1,2,3,4-Tetrahydro-1-(dimethylhydrazono)-7-methoxy-2-naphthaleneacetaldehyde dimethyl acetal (45.0 g) was dissolved under argon in a mixture of 1800 ml of tetrahydrofuran and 645 ml of 0.067M phosphate buffer of pH value 7. The solution was treated with 19.8 g of copper(II) chloride dihydrate and stirred at room temperature for 16 hours. 1000 ml of ethyl acetate were added to the reaction mixture and it was washed three times with 1500 ml of a mixture of 25% ammonia solution and saturated ammonium chloride solution (1:19) each time. The aqueous wash phases were extracted twice with 1000 ml of ethyl acetate, the organic phases were combined, dried over MgSO4 and freed from solvent. There were obtained 39.7 g of crude 1,2,3,4-tetrahydro-7-methoxy-1-oxo-2-naphthaleneacetaldehyde dimethyl acetal which was processed without purification.

Workup

  1. washwas washed three times with 1500 ml of a mixture of 25% ammonia solution and saturated ammonium chloride solution (1:19) each time
  2. extractionThe aqueous wash phases were extracted twice with 1000 ml of ethyl acetate
  3. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-baafceb83db749ab9b835cec769985f2
Source dataset
uspto-grants-1994_03
Patent number
US05292732

Reaction notes

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