p-Toluenesulfonic acid → 4-(Cyclohex-1-EN-1-YL)benzaldehyde

HRID 1884269Notes

Reaction equation

HRID 1884269 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[CH:11]=[CH:10][C:9]([C:12]2(O)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:8][CH:7]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[C:12]1([C:9]2[CH:8]=[CH:7][C:6]([CH:2]=[O:1])=[CH:11][CH:10]=2)[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]=1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 154477571-(4-(1,3-Dioxolan-2-yl)phenyl)cyclohexanol

Product 1

HCID 235088524-(Cyclohex-1-EN-1-YL)benzaldehydeYield 13.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

1-(4-[1,3]Dioxolan-2-yl-phenyl)cyclohexanol (45 g) and p-toluenesulfonic acid (3.4 g) in 300 mL of toluene were refluxed for 3 hours under Dean-Stark conditions. After cooling, ethyl acetate and a saturated sodium hydrogen carbonate solution were added. The organic layer was washed twice with water, dried (magnesium sulphate), filtered and concentrated in vacuo. The residual oil was dissolved in glacial acetic acid (250 mL) and 1 M hydrochloric acid (25 mL) was added and the mixture was stirred at 50° C. for 2 hours. After cooling, the mixture was concentrated in vacuo. The residual oil was partitioned between ethyl acetate and water. The organic phase was washed three times with water, dried (magnesium sulphate), filtered and concentrated in vacuo. The residual oil was distilled in vacuo and the fraction boiling at 120-130° C. (0.2 mmHg) was collected to afford 4.7 g of the title compound.

Workup

  1. temperatureAfter cooling
  2. washThe organic layer was washed twice with water
  3. dry with materialdried (magnesium sulphate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residual oil was dissolved in glacial acetic acid (250 mL)
  7. addition1 M hydrochloric acid (25 mL) was added
  8. temperatureAfter cooling
  9. concentrationthe mixture was concentrated in vacuo
  10. customThe residual oil was partitioned between ethyl acetate and water
  11. washThe organic phase was washed three times with water
  12. dry with materialdried (magnesium sulphate)
  13. filtrationfiltered
  14. concentrationconcentrated in vacuo
  15. distillationThe residual oil was distilled in vacuo
  16. customthe fraction boiling at 120-130° C. (0.2 mmHg) was collected

Sources & evidence

ORD record
ord-d805dbf047d74f90b869cc96ea931ffa
Source dataset
uspto-grants-2004_07
Patent number
US06762318B2

Reaction notes

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