Acetaldehyde → HCID 566606, compound

HRID 1820575Notes

Reaction equation

HRID 1820575 reaction equation
Br[CH:2]1[CH2:9][CH2:8][CH2:7][CH:6]=[CH:5][CH2:4][CH2:3]1.[Mg].[CH:11](=[O:13])[CH3:12].Cl>C(OCC)C>[CH:2]1([C:11](=[O:13])[CH3:12])[CH2:9][CH2:8][CH2:7][CH:6]=[CH:5][CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 313Hydrochloric AcidHCID 5462224MagnesiumHCID 669575615-Bromocyclooct-1-ene

Product 1

HCID 566606HCID 566606, compoundYield 30.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
5 °C

Procedure

A solution of 5-bromo-cyclooctene (5 g, 26 mmol; prepared by treatment of 1,5-cyclooctadiene with HBr in AcOH) in diethyl ether was added to magnesium (0.7 g, 29 mmol, 1.1 eq.). The resulting solution was cooled to 5° C. and treated dropwise with a solution of acetaldehyde (5 ml, 89 mmol, 3.4 eq.) in diethyl ether (10 ml). The resulting mixture was stirred 3 h at 20° C., treated with 2M HCl, and extracted with diethyl ether. The organic phases were washed successively with NaHCO3, NH4Cl and NaCl solutions, and dried (Na2SO4) and the solvent evaporated under vacuum. The crude product was purified by flash chromatography (hexane/Et2O 10:1) to give 1.2 g of 1-cyclooct-4-enylethanone (30%).

Workup

  1. extractionextracted with diethyl ether
  2. washThe organic phases were washed successively with NaHCO3, NH4Cl and NaCl solutions
  3. dry with materialdried (Na2SO4)
  4. customthe solvent evaporated under vacuum
  5. customThe crude product was purified by flash chromatography (hexane/Et2O 10:1)

Sources & evidence

ORD record
ord-27d7ea2090e544408404bed4960341d4
Source dataset
uspto-grants-2009_10
Patent number
US07605118B2

Reaction notes

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