Hydrochloric Acid → HCID 59518507, compound

HRID 1161615Notes

Reaction equation

HRID 1161615 reaction equation
[CH3:1][C:2]1([CH3:10])[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][C:3]1=[O:9].[C:11](C#N)(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH2:21](N(CC)CC)C.Cl>ClCCl.[Cl-].[Zn+2].[Cl-]>[C:11]([CH:4]1[C:5](=[O:8])[CH:6]([CH3:21])[CH2:7][C:2]([CH3:10])([CH3:1])[C:3]1=[O:9])(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 11953PhenylglyoxylonitrileHCID 1363601,3-Cyclohexanedione, 4,4-dimethyl-

Product 1

HCID 59518507HCID 59518507, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Alternatively, the compounds of formula (V) can be prepared according to a second representative procedure, as follows: 4,4-dimethyl-1,3-cyclohexanedione 7 (1 mole eq) (commercially available) and benzoyl cyanide are dissolved in anhydrous dichloromethane and cooled to 0° C. under an atmosphere of nitrogen. To the cooled solution is added anhydrous finely powdered zinc chloride (1.1 mole eq) followed by slow addition of triethylamine (1.2 mole eq). The reaction mixture is stirred at room temperature for 5-6 h and then poured into 2 M hydrochloric acid. The mixture is partitioned and the dichloromethane layer washed with 5% sodium carbonate. The aqueous carbonate phase is then acidified with hydrochloric acid and extracted with methylene chloride and dried (Na2SO4). The solvent is removed and the residue subjected to SiO2 column chromatography (hexane/ethyl acetate) affording 1-benzoyl-3,3,5-trimethylcyclohexan-2,6-dione 8. (W. J. Michaely and G. W. Kraatz, EP-B-135191).

Workup

  1. customThe mixture is partitioned
  2. washthe dichloromethane layer washed with 5% sodium carbonate
  3. extractionextracted with methylene chloride
  4. dry with materialdried (Na2SO4)
  5. customThe solvent is removed

Sources & evidence

ORD record
ord-89f5c6c8eb0944f486165043a792dc7a
Source dataset
uspto-grants-2010_10
Patent number
US07820209B2

Reaction notes

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