Pyridine → 2-[(p-Cyclohexylphenyl)-oxomethyl]-pyridine

HRID 1576337Notes

Reaction equation

HRID 1576337 reaction equation
N1C=CC=CC=1.[CH:7]1([C:13]2[CH:18]=[CH:17][C:16]([CH:19]([OH:26])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)=[CH:15][CH:14]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1>C(Cl)Cl.[O-2].[O-2].[O-2].[Cr+6]>[CH:7]1([C:13]2[CH:18]=[CH:17][C:16]([C:19](=[O:26])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)=[CH:15][CH:14]=2)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1

Participants

5

Reactant 2

HCID 1049PyridineHCID 20310417alpha-(4-Cyclohexylphenyl)-2-pyridinemethanol

Product 1

HCID 203104282-[(p-Cyclohexylphenyl)-oxomethyl]-pyridine

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

10.0 g of chromium trioxide are added in portions at 5°C, whilst stirring and with exclusion of moisture, to a solution of 15.8 ml of pyridine in 200 ml of absolute methylene chloride, behind a protective shield. After the completion of the addition the mixture is stirred for a further 30 minutes at room temperature, 2.8 g of crude 2-[(p-cyclohexylphenyl)-hydroxymethyl]-pyridine, dissolved in 10 ml of methylene chloride, are then added all at once and the mixture is stirred for a further 20 minutes at room temperature. The mixture is decanted off from the brown resin which is formed and is partitioned at 0°C between 50 ml of methylene chloride and 2 lots of 50 ml of saturated sodium bicarbonate solution. The organic phase is washed successively with twice 50 ml of 0.1 N hydrochloric acid and twice 50 ml of water, dried over sodium sulphate and evaporated in vacuo. Chromatography of the evaporation residue on 200 g of silica gel, using chloroform as eluant, and fractional crystallisation from cold ethanol, yields 2-[(p-cyclohexylphenyl)-oxomethyl]-pyridine of the formula ##SPC11##

Workup

  1. additionAfter the completion of the addition the mixture
  2. additionare then added all at once and the mixture
  3. stirringis stirred for a further 20 minutes at room temperature
  4. customThe mixture is decanted off from the brown resin which
  5. customis formed
  6. customis partitioned at 0°C between 50 ml of methylene chloride and 2 lots of 50 ml of saturated sodium bicarbonate solution
  7. washThe organic phase is washed successively with twice 50 ml of 0.1 N hydrochloric acid and twice 50 ml of water
  8. dry with materialdried over sodium sulphate
  9. customevaporated in vacuo
  10. customfractional crystallisation from cold ethanol

Sources & evidence

ORD record
ord-93948792845c4ad08efb2e12defd6539
Source dataset
uspto-grants-1976_09
Patent number
US03980657

Reaction notes

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