Water → 3,3-Diethyl-1,5-dioxaspiro[5.5]undecan-9-one

HRID 342475

Reaction equation

HRID 342475 reaction equation
[C:1]1(=[O:8])[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][CH2:2]1.[CH2:9]([C:11]([CH2:16][CH3:17])([CH2:14]O)[CH2:12][OH:13])[CH3:10].O>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:9]([C:11]1([CH2:16][CH3:17])[CH2:12][O:13][C:4]2([CH2:5][CH2:6][C:1](=[O:8])[CH2:2][CH2:3]2)[O:7][CH2:14]1)[CH3:10]

Participants

6

Reactant 3

HCID 962Water2×HCID 8284PrenderolHCID 125111,4-Cyclohexanedione

Product 1

HCID 676976933,3-Diethyl-1,5-dioxaspiro[5.5]undecan-9-oneYield 16,365.5%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

30 g (0.27 mmol) of cyclohexane-1,4-dione, 35.4 g (0.27 mol) of 2,2-diethylpropane-1,3-diol and 360 mg of para-toluenesulfonic acid were heated in 200 ml of toluene on a water separator. After the mixture had been cooled to room temperature and the water of reaction separated off, the organic phase was washed with a semisaturated sodium hydrogen carbonate solution and dried over magnesium sulfate. After the solvent had been evaporated, 65 g of crude product were obtained which was purified by flash chromatography (ethyl acetate/petroleum ether=1:4). The first fraction contained the 1,4-diketal which was formed as secondary product (10 g). The main fraction contained 28.5 g (47%) of a yellow oil.

Workup

  1. customseparated off
  2. washthe organic phase was washed with a semisaturated sodium hydrogen carbonate solution
  3. dry with materialdried over magnesium sulfate
  4. customAfter the solvent had been evaporated
  5. custom65 g of crude product were obtained which
  6. customwas purified by flash chromatography (ethyl acetate/petroleum ether=1:4)

Sources & evidence

ORD record
ord-0a1588cf774c4fd8a5eee7ad372743fb
Source dataset
uspto-grants-1999_01
Patent number
US05859009

Linked notes

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