Pyridine → 1-(2,2,4-trimethyl-cyclohex-3-enyl)-ethanone O-methyl-oxime

HRID 42729

Reaction equation

HRID 42729 reaction equation
[CH3:1][C:2]1([CH3:12])[CH:7]=[C:6]([CH3:8])[CH2:5][CH2:4][CH:3]1[C:9](=O)[CH3:10].N1C=CC=CC=1.Cl.[CH3:20][O:21][NH2:22]>CO>[CH3:20][O:21][N:22]=[C:9]([CH:3]1[CH2:4][CH2:5][C:6]([CH3:8])=[CH:7][C:2]1([CH3:12])[CH3:1])[CH3:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 30169881-(2,2,4-Trimethyl-3-cyclohexen-1-yl)ethan-1-one

Product 1

HCID 866753381-(2,2,4-trimethyl-cyclohex-3-enyl)-ethanone O-methyl-oximeYield 92.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
24 °C

Procedure

To a stirred solution of 1-(2,2,4-trimethyl-cyclohex-3-enyl)-ethanone (162 g; 0.97 mol), prepared as described in example P4, in methanol (500 ml) was added pyridine (160 ml; 1.95 mol) followed by a portionwise addition of methoxyamine hydrochloride (142 g; 1.70 mol). The reaction mixture was stirred at 24° C. for 16 hours under nitrogen atmosphere. Methanol was removed under reduced pressure, the residue poured in water (600 ml) and 1N hydrochloric acid was added (100 ml). The solution was extracted with dichloromethane (3×300 ml). Combined organic layers were washed with brine (500 ml) and dried over sodium sulfate. The solvent was removed in vacuo to afford 175 g (92% of theory) of 1-(2,2,4-trimethyl-cyclohex-3-enyl)-ethanone O-methyl-oxime as a clear red oil.

Workup

  1. customMethanol was removed under reduced pressure
  2. additionthe residue poured in water (600 ml)
  3. addition1N hydrochloric acid was added (100 ml)
  4. extractionThe solution was extracted with dichloromethane (3×300 ml)
  5. washCombined organic layers were washed with brine (500 ml)
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-949bef1b62f54a69bbcb37a365ea0c46
Source dataset
uspto-grants-2013_09
Patent number
US08536215B2

Linked notes

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