Thionyl Chloride → HCID 15324703, compound

HRID 861866Notes

Reaction equation

HRID 861866 reaction equation
[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][C:16]([OH:18])=O)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)(Cl)=O>N1C=CC=CC=1.C1(C)C=CC=CC=1>[CH:1]1([C:7]2[CH:8]=[C:9]3[C:10]([CH2:13][CH2:14][CH2:15][C:16]3=[O:18])=[CH:11][CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 3041568Benzenebutanoic acid, 4-cyclohexyl-

Product 1

HCID 15324703HCID 15324703, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 1140TolueneSolvent

Procedure

To a mixture of 4-(4-cyclohexylphenyl)butyric acid (10.2 g), thionyl chloride (7.4 g) and toluene (50 ml), pyridine (1 drop) was added. After refluxing for 1.5 hours, the solvent was evaporated off under reduced pressure. The residue was dissolved in dichloromethane (20 ml); this solution was added dropwise to a suspension of powdered anhydrous aluminum chloride (8.3 g) in dichloromethane (100 ml) under ice cooling conditions. After stirring at room temperature for 3 hours, the reaction mixture was poured into 1.2N HCl (150 ml), followed by stirring for 30 minutes. The organic layer was collected, while the aqueous layer was extracted with dichloromethane. The extract was combined with the organic layer, succesively washed with water and brine, and dried (MgSO4), after which the solvent was evaporated off. The residual oil was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (1:10, v/v) to yield 7-cyclohexyl-1-tetralone (9.4 g, 100%) as an oil.

Workup

  1. additionwas added
  2. temperatureAfter refluxing for 1.5 hours
  3. customthe solvent was evaporated off under reduced pressure
  4. dissolutionThe residue was dissolved in dichloromethane (20 ml)
  5. additionthis solution was added dropwise to a suspension of powdered anhydrous aluminum chloride (8.3 g) in dichloromethane (100 ml) under ice cooling conditions
  6. additionthe reaction mixture was poured into 1.2N HCl (150 ml)
  7. stirringby stirring for 30 minutes
  8. customThe organic layer was collected, while the aqueous layer
  9. extractionwas extracted with dichloromethane
  10. washsuccesively washed with water and brine
  11. dry with materialdried (MgSO4)
  12. customafter which the solvent was evaporated off
  13. washeluted with ethyl acetate-hexane (1:10

Sources & evidence

ORD record
ord-bcb888925d7a44688ee78799509725b8
Source dataset
uspto-grants-1998_02
Patent number
US05716944

Reaction notes

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