Water → HCID 86644172, compound

HRID 1927660Notes

Reaction equation

HRID 1927660 reaction equation
[F:1][CH2:2][C:3]([CH2:9][F:10])([CH2:7][CH3:8])[CH2:4][CH:5]=C.O.I([O-])(=O)(=O)=[O:13].[K+]>CC(C)=O.C(OCC)C.[Os](=O)(=O)(=O)=O>[F:1][CH2:2][C:3]([CH2:9][F:10])([CH2:7][CH3:8])[CH2:4][CH:5]=[O:13]

Participants

7

Reactant 3

HCID 962WaterHCID 516896Potassium periodateHCID 86644173HCID 86644173, compound

Product 1

HCID 86644172HCID 86644172, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 4,4-bis(fluoromethyl)hex-1-ene (9.1 g, 62 mmol) in acetone (360 mL)/water (120 mL) at rt was added osmium tetroxide (155 mg, 0.62 mmol) and potassium periodate (29.7 g; 129 mmol) (the latter in portions). After stirring for 15 h, the reaction mixture was diluted with diethyl ether (180 mL). The organic layer was separated, and the aqueous layer was extracted with diethyl ether (3×180 mL). The extracts were washed with saturated sodium thiosulfate (250 mL) and brine (250 mL), dried over sodium sulfate and concentrated to give a residue. The resulting residue was distilled under vacuum to provide 3,3-bis(fluoromethyl)pentanal.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with diethyl ether (3×180 mL)
  3. washThe extracts were washed with saturated sodium thiosulfate (250 mL) and brine (250 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customto give a residue
  7. distillationThe resulting residue was distilled under vacuum

Sources & evidence

ORD record
ord-fe35be8fd43d404db47d038b8b264c29
Source dataset
uspto-grants-2012_05
Patent number
US08183275B2

Reaction notes

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