Ethyl Acetate → HCID 19095362, compound

HRID 486547Notes

Reaction equation

HRID 486547 reaction equation
[CH3:1][O:2][CH:3]([O:20][CH3:21])[CH2:4][CH:5]1[CH2:14][CH:13]([CH3:15])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][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][CH:13]([CH3:15])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:24]

Participants

6

Reactant 2

HCID 8857Ethyl AcetateHCID 67850256HCID 67850256, compound

Product 1

HCID 19095362HCID 19095362, compound

Reagents, catalysts & solvents 3

HCID 61482Cupric chloride dihydrateCatalystHCID 1061PhosphateSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-(Dimethylhydrazono)-1,2,3,4-tetrahydro-4-methyl-2-naphthaleneacetaldehyde dimethyl acetal (23.1 g) was dissolved under argon in a mixture of 1000 ml of tetrahydrofuran and 350 ml of 0.067M phosphate buffer of pH value 7. The solution was treated with 13.6 g of copper(II) chloride dihydrate and stirred at room temperature for 16 hours. 500 ml of ethyl acetate were added to the reaction mixture and it was washed three times with a mixture of 25% ammonia solution and saturated ammonium chloride solution (1:19) (1×800 ml, 2×500 ml). The aqueous wash phases were extracted twice with 500 ml of ethyl acetate each time, the organic phases were combined, dried over MgSO4 and freed from solvent. There were obtained 20.0 g of crude 1,2,3,4-tetrahydro-4-methyl-1-oxo-2-naphthaleneacetaldehyde dimethyl acetal which was processed without purification.

Workup

  1. washwas washed three times
  2. additionwith a mixture of 25% ammonia solution and saturated ammonium chloride solution (1:19) (1×800 ml, 2×500 ml)
  3. extractionThe aqueous wash phases were extracted twice with 500 ml of ethyl acetate each time
  4. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-51d6175de9af434eb68f92fb737151fc
Source dataset
uspto-grants-1994_03
Patent number
US05292732

Reaction notes

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