Water → Cyclooctanone

HRID 991271Notes

Reaction equation

HRID 991271 reaction equation
[CH:1]1([OH:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O.C1(C)C=CC=CC=1.[OH-].[Na+]>CN1CCCC1=O>[C:1]1(=[O:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 12766CyclooctanolHCID 14798Sodium Hydroxide

Product 1

HCID 10403CyclooctanoneYield 71.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

10.6 g of stabilized IBX prepared as in Example 10 are suspended in 60 ml of N-methylpyrrolidone at 20° C., and 2 g of cyclooctanol are added dropwise while maintaining the temperature at from 20° C. to 25° C. After 2 hours, agitation, the medium is poured into a mixture of 130 ml of water and 80 ml of toluene; the pH of the aqueous phase is brought to approximately 7 by the addition of aqueous NaOH and the organic phase, after separation of the insoluble material formed and of the aqueous phase, is concentrated to give 1.4 g of pure cyclooctanone (NMR and GPC)

Workup

  1. custom10.6 g of stabilized IBX prepared as in Example 10
  2. temperaturewhile maintaining the temperature at from 20° C. to 25° C
  3. customthe organic phase, after separation of the insoluble material
  4. customformed and of the aqueous phase
  5. concentrationis concentrated

Sources & evidence

ORD record
ord-4ea1944d37164d8fb9561bcfa9f7b1be
Source dataset
uspto-grants-2002_10
Patent number
US06462227B2

Reaction notes

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