2-Propanone, 1-(1-oxopropoxy)- → HCID 24885943, compound

HRID 1821142Notes

Reaction equation

HRID 1821142 reaction equation
[CH3:1][C:2]1([CH2:20][O:21][C:22](=[O:25])[CH2:23][CH3:24])[O:7][CH2:6][C:5]([CH2:14]OC(=O)CC)([CH2:8][O:9]C(=O)CC)[CH2:4][O:3]1.[C:26]([O:30][CH2:31][C:32](=[O:34])[CH3:33])(=[O:29])[CH2:27][CH3:28]>>[CH3:1][C:2]1([CH2:20][O:21][C:22](=[O:25])[CH2:23][CH3:24])[O:7][CH2:6][C:5]2([CH2:8][O:9][C:32]([CH3:33])([CH2:31][O:30][C:26](=[O:29])[CH2:27][CH3:28])[O:34][CH2:14]2)[CH2:4][O:3]1

Participants

3

Reactant 2

HCID 30858602-Propanone, 1-(1-oxopropoxy)-HCID 69066448HCID 69066448, compound

Product 1

HCID 24885943HCID 24885943, compoundYield 53%

Procedure

A solution of propionyloxyacetone (10 g, 76.8 mmol), pentaerythritol (5.22 g, 38.4 mmol), and pyridinium p-toluenesulfonate (1.0 g, 4 mmol) in toluene (200 ml) was stirred under reflux for 6 hours, while water was removed using a Dean-Stark water separator. After cooling to room temperature, the reaction liquid was poured into ethyl acetate (300 ml)/an aqueous sodium hydrogencarbonate solution (350 ml). After phase separation, the organic layer was washed twice with water (200 ml), and once with saturated brine (200 ml), and then dried over sodium sulfate. After the sodium sulfate was filtered out, the solvent was distilled off under reduced pressure, to obtain 11.0 g of a concentrate residue. As a result of measurement of NMR spectra of the concentrate residue, it was found that the by-product of Comparative Example 1 (2-methyl-2,5,5-tris(propionyloxymethyl)-[1,3]dioxane) was hardly detected, while other by-products were formed, and that the starting material propionyloxyacetone remained at a similar level to that in Comparative Example 1. The concentrate residue was purified by column chromatography (eluent: ethyl acetate/hexane=1/2), to give 3,9-dimethyl-3,9-bis(propionyloxymethyl)-2,4,8,10-tetraoxaspiro[5,5]undecane (7.3 g, 20.3 mmol, yield 53%).

Workup

  1. customAs a result of measurement of NMR spectra of the concentrate residue, it
  2. customwere formed
  3. customThe concentrate residue was purified by column chromatography (eluent: ethyl acetate/hexane=1/2)

Sources & evidence

ORD record
ord-b34630f1d3634fee8c85704ab752c513
Source dataset
uspto-grants-2009_10
Patent number
US07605276B2

Reaction notes

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