Water → HCID 1487265, compound

HRID 1089115Notes

Reaction equation

HRID 1089115 reaction equation
[CH2:1]1[O:11][C:4]2([CH2:9][CH2:8][C:7](=O)[CH2:6][CH2:5]2)[O:3][CH2:2]1.[C:12]1([NH:18]N)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.S([O-])([O-])(=O)=O.[Mg+2].O>C(Cl)Cl.[Cl-].[Zn+2].[Cl-]>[CH2:2]1[CH2:1][O:11][C:4]2([CH2:9][C:8]3[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[NH:18][C:7]=3[CH2:6][CH2:5]2)[O:3]1

Participants

7

Reactant 4

HCID 962WaterHCID 7516PhenylhydrazineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 5674151,4-Dioxaspiro[4.5]decan-8-one

Product 1

HCID 1487265HCID 1487265, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

77.2 g (0.5 mol) of 1,4-cyclohexanedione monoethylene ketal are dissolved together with 48.4 ml (0.5 mol) of phenylhydrazine in 2 l of methylene chloride, and 300 g of magnesium sulphate are added, and the mixture is stirred for 30 min. The magnesium sulphate is then filtered off with suction, washed with methylene chloride, and the filtrate is evaporated. The residue is taken up in 1.5 l of benzene, and 62.1 g (0.46 mol) of anhydrous zinc chloride are added and the mixture is heated under reflux with a water separator for 3 h. The reaction solution is then concentrated, 2N sodium hydroxide solution is added, and the mixture is extracted 3 times with ethyl acetate. The combined ethyl acetate phases are dried with sodium sulphate and evaporated. The residue crystallizes from a little ether. In this way 3.5 g (72% of theory) of the product are obtained.

Workup

  1. additionare added
  2. filtrationThe magnesium sulphate is then filtered off with suction
  3. washwashed with methylene chloride
  4. customthe filtrate is evaporated
  5. temperaturethe mixture is heated
  6. waitseparator for 3 h
  7. concentrationThe reaction solution is then concentrated
  8. addition2N sodium hydroxide solution is added
  9. extractionthe mixture is extracted 3 times with ethyl acetate
  10. dry with materialThe combined ethyl acetate phases are dried with sodium sulphate
  11. customevaporated
  12. customThe residue crystallizes from a little ether
  13. customIn this way 3.5 g (72% of theory) of the product are obtained

Sources & evidence

ORD record
ord-4ae42e8415054dcaa37a42844a7eebec
Source dataset
uspto-grants-1990_10
Patent number
US04965258

Reaction notes

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