O-Xylene → HCID 19363368, compound

HRID 850416Notes

Reaction equation

HRID 850416 reaction equation
NN[C:3](N)=O.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11](C)=[CH:10][C:9]=1C(CCCCCC)C=O.[CH3:24][C:25]([CH3:28])([O-])[CH3:26].[K+].[C:30]1(C)[C:31](C)=[CH:32]C=[CH:34][CH:35]=1>>[CH3:24][C:25]([C:28]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:8][O:7][CH3:6])([CH3:3])[CH2:26][CH2:34][CH2:35][CH2:30][CH2:31][CH3:32]

Participants

4

Reactant 3

HCID 7237O-XyleneHCID 19363503HCID 19363503, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 19363368HCID 19363368, compound

Procedure

2-(2-Methoxy-5-methylphenyl)octanal semicarbazide (64.7 g, 0.203 mol), potassium t-butoxide (47.8 g, 0.43 mol) and xylene (600 ml) were mixed, and this solution was refluxed under heating for 2.5 hours. This reaction mixture was poured into ice water (200 ml) to stop the reaction. The aqueous layer was extracted 3 times with toluene (120 ml). The organic layer was washed 3 times with saturated brine (100 ml) and dried over anhydrous magnesium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography (chloroform) to give 2-(1,1-dimethylheptyl)-1-methoxymethylbenzene (51 g, overweight) as a mixture with xylene. The mixture was used for the next reaction.

Workup

  1. temperaturethis solution was refluxed
  2. temperatureunder heating for 2.5 hours
  3. customthe reaction
  4. extractionThe aqueous layer was extracted 3 times with toluene (120 ml)
  5. washThe organic layer was washed 3 times with saturated brine (100 ml)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationThe drying agent was filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe obtained residue was purified by column chromatography (chloroform)

Sources & evidence

ORD record
ord-d0c67137762b4c8683f046a068503440
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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