Diethyl Ether → 2-Ethylcyclohexanone

HRID 247644

Reaction equation

HRID 247644 reaction equation
[CH2:1]([CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[OH:9])[CH3:2].C(O)(C)C.CCOCC>CC(C)=O.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>[CH2:1]([CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=[O:9])[CH3:2]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 3776IsopropanolHCID 195762-Ethylcyclohexanol

Product 1

HCID 204742-EthylcyclohexanoneYield 91.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 131709961Jones' reagentSolvent

Procedure

2-Ethylcyclohexanol (1.6 moles, 204 g, 226 mL) was stirred in 3.2 L of acetone at 0° C. and treated with 8N Jones reagent (prepared from 106.8 g of CrO3 suspended in 92 mL of concentrated sulfuric acid and diluted to 400 mL with water) until the orange color persisted (~430 mL). Isopropanol was then added to turn the solution green again after which it was poured into 2 L of ether. The product was washed with 6×500 mL of brine, dried over MgSO4 and stripped of solvent. Short path distillation (b.p. 80°-85° C. at 25 mm) afforded 184 g (1.46 moles, 91%) of 2-ethylcyclohexanone as a colorless oil.

Workup

  1. washThe product was washed with 6×500 mL of brine
  2. dry with materialdried over MgSO4
  3. distillationShort path distillation (b.p. 80°-85° C. at 25 mm)

Sources & evidence

ORD record
ord-e6bc06c169574e59bb12853bb3bafd88
Source dataset
uspto-grants-1987_11
Patent number
US04709048

Linked notes

Loading…