Acetonitrile → HCID 19086759, compound

HRID 1464561Notes

Reaction equation

HRID 1464561 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]([O:13][CH:14]([F:16])[F:15])[CH:10]=[CH:9][C:5]=1[C:6](Cl)=[O:7])([O-:3])=[O:2].[CH3:17][C:18]1([CH3:27])[CH2:23][CH:22]([CH3:24])[C:21](=[O:25])[CH2:20][C:19]1=[O:26].C(#N)C.CC(C)(O)C#N>Cl.C(N(CC)CC)C>[N+:1]([C:4]1[CH:12]=[C:11]([O:13][CH:14]([F:16])[F:15])[CH:10]=[CH:9][C:5]=1[C:6]([CH:20]1[C:19](=[O:26])[C:18]([CH3:17])([CH3:27])[CH2:23][CH:22]([CH3:24])[C:21]1=[O:25])=[O:7])([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 6406Acetone CyanohydrinHCID 147495764,4,6-Trimethylcyclohexane-1,3-dioneHCID 19086761HCID 19086761, compound

Product 1

HCID 19086759HCID 19086759, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8471TriethylamineSolvent

Procedure

5.03 g of 2-nitro-4-difluoromethoxybenzoyl chloride and 2.57 g of 4,4,6-trimethylcyclohexane-1,3-dione are introduced into 20 ml of acetonitrile, and 4.21 g of triethylamine are added dropwise in such a way that the internal temperature does not exceed 40° C. The mixture is subsequently stirred for 15 minutes at room temperature, 1.29 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 acetates and 50 ml of 1N hydrochloric acid are added. After vigorous shaking, the phases are separated, the organic phases are dried over MgSO4, and the solvent is stripped off under reduced pressure. The oil which remains (7.1 g) is chromatographed on silica gel using ethyl acetate/petroleum ether 1:2 as the eluent. This gives 3.28 g (46% of theory) of 2-(2-nitro-4-difluoromethoxy-benzoyl)-4,4,6-trimethylcyclohexane-1,3-dione of melting point 108°-110° C.

Workup

  1. additionare added dropwise in such a way 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. dry with materialthe organic phases are dried over MgSO4
  8. customis chromatographed on silica gel

Sources & evidence

ORD record
ord-c0d6e47509ab406f8f89d8407c340ab5
Source dataset
uspto-grants-1994_04
Patent number
US05306695

Reaction notes

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