Hydrochloric Acid → HCID 66747893, compound

HRID 1464899Notes

Reaction equation

HRID 1464899 reaction equation
[CH2:1]([C:5]1[CH2:10][CH:9]([CH3:11])[C:8]([CH:13]([OH:15])[CH3:14])([CH3:12])[CH2:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.Cl>CN(C)C=O>[CH2:1]([C:5]1[CH2:10][CH:9]([CH3:11])[C:8]([C:13](=[O:15])[CH3:14])([CH3:12])[CH2:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2724130Cornforth reagent2×HCID 66747180HCID 66747180, compound

Product 1

HCID 66747893HCID 66747893, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(4-Isobutyl-1,6-dimethylcyclohex-3-enyl)ethanol 4d (2 g, 9 mmol) was dissolved in dimethylformamide (50 ml) and cooled to below 5° C. under nitrogen. Pyridinium dichromate (4.5 g, 12 mmol) was added in two portions with stirring and the reaction allowed to return to room temperature. After stirring for 90 min another portion of PDC (1 g, 2.7 mmol) was added and after a further 90 min the reaction was complete. The reaction mixture was poured onto ice-water and 2M HCl added. After brief agitation the product was extracted from the aqeuous phase with MTBE. The organic phases were combined and washed with sat. NaHCO3 solution then to pH 7 with brine. After drying (Na2SO4) the solvent was removed in vacuo to give 1.8 g of a crude oil which was purified by flash chromatography (MTBE/hexane 2:8). Combination of pure fractions gave 3d as a 7:3 mixture of diastereomers (1.5 g, 77% yield, 99% pure). Subsequent distillation provided a sample for olfactory assessment.

Workup

  1. temperaturecooled to below 5° C. under nitrogen
  2. customto return to room temperature
  3. additionwas added and after a further 90 min the reaction
  4. additionadded
  5. extractionAfter brief agitation the product was extracted from the aqeuous phase with MTBE
  6. washwashed with sat. NaHCO3 solution
  7. dry with materialAfter drying (Na2SO4) the solvent
  8. customwas removed in vacuo
  9. customto give 1.8 g of a crude oil which
  10. customwas purified by flash chromatography (MTBE/hexane 2:8)

Sources & evidence

ORD record
ord-5c9604476be648bfb19e06f6b04c2452
Source dataset
uspto-grants-2015_04
Patent number
US08999914B2

Reaction notes

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