2,4-Dichlorobenzoic Acid → HCID 44479141, compound
Reaction equation
[C:1]1(=[N:7][OH:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:9][C:10]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:11]=1[C:12]([OH:14])=[O:13]>C(Cl)Cl>[Cl:9][C:10]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:11]=1[C:12]([O:14][C:1]1([N:7]=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:13]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
1-Nitrosocyclohexyl 2,4-dichlorobenzoate was prepared according to General Method 3. A solution of cyclohexanone oxime (2.66 g, 23.5 mmol) in DCM (50 ml) was added dropwise to a solution of lead tetra acetate (10.42 g, 23.5 mmol) and 2,4 dichlorobenzoic acid (45.0 g, 235 mmol) in DCM (300 ml) at 0° C. A blue color gradually appears on addition of the oxime solution. Upon complete addition (1 hour) the reaction was allowed to warm to ambient temperature and stirring was continued for a further 2-3 hours. The reaction was quenched by the addition of water, the phases separated and the organics dried over Na2SO4 and concentrated in vacuo to afford 1-nitrosocyclohexyl 2,4-dichlorobenzoate which was purified by column chromatography on silica gel with hexane:EtOAc as the eluent to afford the title compound as a blue oil in 9% yield. δH (400MHz, DMSO-d6) δ 8.02 (1H, d, 8.4 Hz), 7.85 (1H, d, 2.0 Hz), 7.64 (1H, dd, 8.4, 2.0 Hz), 2.03-2.12(2H, m), 1.38-1.93 (8H, m).
Workup
- custom1-Nitrosocyclohexyl 2,4-dichlorobenzoate was prepared
- additionUpon complete addition (1 hour) the reaction
- customThe reaction was quenched by the addition of water
- customthe phases separated
- dry with materialthe organics dried over Na2SO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-47dec6aa2c31475f97ca44d4cee6ff52
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08791134B2
Reaction notes
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