Acetonitrile → HCID 19086758, compound

HRID 1464560Notes

Reaction equation

HRID 1464560 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([O:11][CH:12]([F:14])[F:13])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[C:15]1(=[O:22])[CH2:20][CH2:19][CH2:18][C:17](=[O:21])[CH2:16]1.C(#N)C.CC(C)(O)C#N>C(OCC)(=O)C.Cl.C(N(CC)CC)C>[Cl:1][C:2]1[CH:10]=[C:9]([O:11][CH:12]([F:14])[F:13])[CH:8]=[CH:7][C:3]=1[C:4]([CH:16]1[C:17](=[O:21])[CH2:18][CH2:19][CH2:20][C:15]1=[O:22])=[O:5]

Participants

8

Reactant 4

HCID 6342AcetonitrileHCID 6406Acetone CyanohydrinHCID 104341,3-CyclohexanedioneHCID 19086757HCID 19086757, compound

Product 1

HCID 19086758HCID 19086758, compoundYield 87.3%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

7.23 g of 2-chloro-4-difluoromethoxybenzoyl chloride and 2.80 g of 1,3-cyclohexanedione are introduced into 30 ml of acetonitrile, and 6.32 g of triethylamine is added dropwise in such a manner that the internal temperature does not exceed 40° C. The mixture is subsequently stirred for 15 minutes at room temperature, 1.95 g of acetone cyanohydrin are added, and stirring is continued for 3 hours at room temperature. The reaction mixture is diluted with 100 ml of ethyl acetate and 50 ml of 1N hydrochloric acid are added. After vigorous shaking, the phases are separated, and the organic phase is extracted twice with 50 ml portions of 5% strength potassium carbonate solution. The combined aqueous phases are acidified using concentrated hydrochloric acid and reextracted using dichloromethane (2 times 50 ml). The mixture is dried over magnesium sulfate, the solvent is stripped off, and 6.9 g (87% of theory) of 2-(2-chloro-4-difluoromethoxybenzoyl)-cyclohexane-1,3-dione are then obtained as pale yellow crystals of melting point 68°-72° C.

Workup

  1. additionis added dropwise in such a manner that the internal temperature
  2. customdoes not exceed 40° C
  3. stirringstirring
  4. waitis continued for 3 hours at room temperature
  5. additionare added
  6. customAfter vigorous shaking, the phases are separated
  7. extractionthe organic phase is extracted twice with 50 ml portions of 5% strength potassium carbonate solution
  8. dry with materialThe mixture is dried over magnesium sulfate

Sources & evidence

ORD record
ord-eb8a170ce2de4514a12da8f278078a74
Source dataset
uspto-grants-1994_04
Patent number
US05306695

Reaction notes

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