Diethyl Ether → Acetaldehyde

HRID 635359Notes

Reaction equation

HRID 635359 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:9]2([C:13]#N)CCC2)[CH:5]=[CH:6][C:7]=1Cl.C([Mg]Cl)C1C=CC=CC=1.C(Cl)C1C=CC=CC=1.[Mg].[CH3:33][CH2:34][O:35]CC>C1(C)C=CC=CC=1>[CH:34](=[O:35])[CH3:33].[C:4]1([CH2:9][CH:13]=[O:35])[CH:5]=[CH:6][CH:7]=[CH:2][CH:3]=1

Participants

8

Reactant 5

HCID 3283Diethyl EtherHCID 7503Benzyl ChlorideHCID 5462224MagnesiumHCID 108571341-(3,4-Dichlorophenyl)-1-cyclobutane-carbonitrileHCID 178418336HCID 178418336, compound

Product 2

HCID 177AcetaldehydeHCID 998Phenylacetaldehyde

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1-(3,4-dichlorophenyl)cyclobutanecarbonitrile (6.56 g) in toluene (100 ml) was added dropwise under nitrogen to a stirred solution of benzylmagnesium chloride [prepared in the usual manner from benzyl chloride (5 ml) and magnesium (1.08 g)] in ether (100 ml). When the addition was complete, ether was distilled from the mixture until the internal temperature rose to 95° C., then the mixture was stirred at this temperature for 19 h, cooled to ambient temperature, and quenched by the dropwise addition of water (30 ml) followed by concentrated hydrochloric acid (10 ml). The mixture was stirred at 95° C. for 2.5 hours, then it was cooled to ambient temperature. The organic phase was separated, washed with water (2×100 ml) and saturated brine (100 ml), dried (Na2SO4), and the solvent was removed in vacuo. The residue was purified via flash chromatography over silica using a 5:95 mixture of ethyl acetate and toluene as eluant. Appropriate fractions were combined and the solvents removed in vacuo to give 1-[1-(3,4-dichlorophenyl)cyclobutyl]-2-phenyl)ethanone]-2-phenylethanone as a colourless oil (5.08 g) which solidified slowly at ambient temperature to give a colourless solid, m.p. 53-55° C.

Workup

  1. additionWhen the addition
  2. distillationether was distilled from the mixture until the internal temperature
  3. customrose to 95° C.
  4. customquenched by the dropwise addition of water (30 ml)
  5. stirringThe mixture was stirred at 95° C. for 2.5 hours
  6. temperatureit was cooled to ambient temperature
  7. customThe organic phase was separated
  8. washwashed with water (2×100 ml) and saturated brine (100 ml)
  9. dry with materialdried (Na2SO4)
  10. customthe solvent was removed in vacuo
  11. customThe residue was purified via flash chromatography over silica using
  12. additiona 5:95 mixture of ethyl acetate and toluene as eluant
  13. customthe solvents removed in vacuo

Sources & evidence

ORD record
ord-6a50758b034c48b6a95f99c0a69c9b38
Source dataset
uspto-grants-2001_02
Patent number
US06187802B1

Reaction notes

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