Toluene → 2-(4-(4-Oxocyclohexyl)cyclohexyl)-5-n-butyl-1,3-dioxane

HRID 2119279Notes

Reaction equation

HRID 2119279 reaction equation
C1(C)C=CC=CC=1.[O:8]=[C:9]1[CH2:14][CH2:13][CH:12]([CH:15]2[CH2:20][CH2:19][CH:18]([CH:21]=[O:22])[CH2:17][CH2:16]2)[CH2:11][CH2:10]1.[CH2:23]([CH:27]([CH2:30]O)[CH2:28][OH:29])[CH2:24][CH2:25][CH3:26].C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[O:8]=[C:9]1[CH2:10][CH2:11][CH:12]([CH:15]2[CH2:20][CH2:19][CH:18]([CH:21]3[O:29][CH2:28][CH:27]([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:30][O:22]3)[CH2:17][CH2:16]2)[CH2:13][CH2:14]1

Participants

6

Reactant 4

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 27952592-n-Butylpropane-1,3-diolHCID 121355814-(4-Oxocyclohexyl)cyclohexanecarbaldehyde

Product 1

HCID 234403882-(4-(4-Oxocyclohexyl)cyclohexyl)-5-n-butyl-1,3-dioxaneYield 10.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 300 ml of toluene were added 20.2 g (97.0 mmol) of the 4-(4-oxocyclohexyl)cyclohexanecarbaldehyde described above, 12.8 g (96.8 mmol) of 2-n-butyl-1,3-propanediol, and 1 g of p-toluenesulfonic acid, and the mixture was refluxed by using a Dean-Stark for 2 hours. Water in an amount of 200 ml was added to the reaction solution, the product thus formed was extracted with toluene, the extract was washed with saturated aqueous bicarbonate solution and water in this turn, and then the solvent was distilled off. After the residue was purified by column chromatography on silica gel (eluent: heptane/ethyl acetate=5/1), the solvent was distilled off. The residue was Silo recrystallized from ethanol to give 3.2 g (9.9 mmol) of 2-(4-(4-oxocyclohexyl)-cyclohexyl)-5-n-butyl-1,3-dioxane. Yield of this compound based on 4-(4-oxocyclohexyl)cyclohexanecarbaldehyde was 10%.

Workup

  1. temperaturethe mixture was refluxed
  2. customfor 2 hours
  3. customthe product thus formed
  4. extractionwas extracted with toluene
  5. washthe extract was washed with saturated aqueous bicarbonate solution and water in this turn
  6. distillationthe solvent was distilled off
  7. customAfter the residue was purified by column chromatography on silica gel (eluent: heptane/ethyl acetate=5/1)
  8. distillationthe solvent was distilled off
  9. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-cc35a6cc6fde456f815653fcc5ae3f0e
Source dataset
uspto-grants-2004_02
Patent number
US06685995B1

Reaction notes

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