1,4-Dioxane hydrochloride → 7,7,7-Trifluoro-4-oxo-heptanal

HRID 397961Notes

Reaction equation

HRID 397961 reaction equation
[O:1]1CCO[CH:2]1[CH2:6][CH2:7][C:8](=[O:15])[CH2:9][CH2:10][C:11]([F:14])([F:13])[F:12].Cl.O1CCOCC1>C(=O)(O)[O-].[Na+]>[F:12][C:11]([F:13])([F:14])[CH2:10][CH2:9][C:8](=[O:15])[CH2:7][CH2:6][CH:2]=[O:1]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 225073011-[1,3]Dioxolan-2-yl-6,6,6-trifluoro-hexan-3-one

Product 1

HCID 225072607,7,7-Trifluoro-4-oxo-heptanalYield 69%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

Crude 1-[1,3]dioxolan-2-yl-6,6,6-trifluoro-hexan-3-one (18 g, prepared above) in 1:1 2N HCl-dioxane (80 ml) was heated to reflux for 20 minutes, then neutralized with aqueous sodium bicarbonate (100 ml), then extracted with ethyl acetate (3×75 ml). The combined organics were washed with brine (2×50 ml), then concentrated under reduced pressure to provide crude 7,7,7-trifluoro-4-oxo-heptanal (10 g), which may be used without further purification. 1H NMR (CDCl3) δ9.80 (1H, s), 2.85-2.70 (6H, m), 2.47-2.35 (2H, m).

Workup

  1. temperatureto reflux for 20 minutes
  2. extractionextracted with ethyl acetate (3×75 ml)
  3. washThe combined organics were washed with brine (2×50 ml)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-099660c8df9b4a35aaac00ee5b99c501
Source dataset
uspto-grants-2003_08
Patent number
US06610730B2

Reaction notes

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