Diethyl Ether → (1-Ethylcyclohexyl)acetaldehyde

HRID 1820315Notes

Reaction equation

HRID 1820315 reaction equation
C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1.[CH2:16]([C:18]1([CH2:24][CH2:25][OH:26])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[CH3:17].CC1(C)N([O])C(C)(C)CCC1.C(OCC)C>C(Cl)Cl>[CH2:16]([C:18]1([CH2:24][CH:25]=[O:26])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1)[CH3:17]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 2724126TempoHCID 12217721Iodo benzene diacetateHCID 231099022-(1-Ethylcyclohexyl)ethanol

Product 1

HCID 45091813(1-Ethylcyclohexyl)acetaldehydeYield 220.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

After adding iodobenzene diacetate (1.61 g, 4.98 mmol) to a solution of 2-(1-ethylcyclohexyl)ethanol (708 mg, 4.53 mmol) in methylene chloride (15 mL) at room temperature, 2,2,6,6-tetramethylpiperidine 1-oxyl free radical (70.8 mg, 0.450 mmol) was added and the mixture was stirred for 15 hours. Diethyl ether was added to the reaction mixture, which was then washed with 10% aqueous sodium thiosulfate, 1N hydrochloric acid and saturated aqueous sodium hydrogencarbonate in that order. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to obtain the title compound as an orange oil (1.54 g).

Workup

  1. washwas then washed with 10% aqueous sodium thiosulfate, 1N hydrochloric acid and saturated aqueous sodium hydrogencarbonate in that order
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-adbc7d5bb83a4ccba4c03f9e2bdb21e3
Source dataset
uspto-grants-2009_10
Patent number
US07601843B2

Reaction notes

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