Cyclobutanone → Cyclopropanemethanol

HRID 968424Notes

Reaction equation

HRID 968424 reaction equation
[CH:1]1([OH:5])[CH2:4][CH2:3][CH2:2]1.[C:6]1(=[O:10])[CH2:9][CH2:8][CH2:7]1>Cl>[CH:1]1([OH:5])[CH2:4][CH2:3][CH2:2]1.[CH:9]1([CH2:6][OH:10])[CH2:7][CH2:8]1

Participants

5

Reactant 2

HCID 14496Cyclobutanone2×HCID 76218Cyclobutanol

Product 2

HCID 75644CyclopropanemethanolHCID 76218Cyclobutanol

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

The processes so far described for the oxidation of cyclobutanol to cyclobutanone use customary oxidizing agents in organic synthesis. A comparison of the existing oxidation methods is given in DE 199 10 464. In general, these are oxidations carried out in homogeneous systems from which the desired cyclobutanone first has to be isolated by extraction or the like. These processes generally lead to large amounts of waste and also to high burdens of toxic reagents, for example when using CrO3/oxalic acid according to Org. Synth. 1981, 60, 20–25. In this process, the direct oxidation of the solution of cyclobutanol in aqueous hydrochloric acid obtained from the isomerization of cyclopropylmethanol is described. For the conversion of 49.5 g of cyclopropylmethanol (results in 14–16 g of cyclobutanone, yield 31–35%), approximately 1.2 l of strongly acidic, chromium-containing wastewater is formed.

Workup

  1. customin organic synthesis
  2. customto be isolated by extraction

Sources & evidence

ORD record
ord-adfe3a44ec204c338702e39b73d64f7b
Source dataset
uspto-grants-2005_10
Patent number
US06958421B2

Reaction notes

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