Diethyl Ether → 1-Acetyl-1-(3,4-dichlorophenyl)cyclobutane

HRID 266882

Reaction equation

HRID 266882 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2(C#N)[CH2:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].C[Mg]I.CC[O:20][CH2:21][CH3:22]>>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:21](=[O:20])[CH3:22])[CH2:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 3

HCID 3283Diethyl Ether2×HCID 108571341-(3,4-Dichlorophenyl)-1-cyclobutane-carbonitrileHCID 178418373HCID 178418373, compound

Product 1

HCID 130831391-Acetyl-1-(3,4-dichlorophenyl)cyclobutane

Procedure

A solution of 1-(3,4-dichlorophenyl)cyclobutanecarbonitrile (163.6 g) in ether (130 ml) was added dropwise over 0.5 hours at ambient temperature under nitrogen to stirred methylmagnesium iodide (3M solution in ether; 300 ml), then the mixture was heated under reflux for 1 hour, diluted with ether (100 ml), heated under reflux for a further 2.5 hours, then stirred at ambient temperature for 18 hours. The resulting solid was collected by filtration, washed well with ether, and added in portions at <20° C. to a stirred mixture of concentrated hydrochloric acid (410 ml) and water (650 ml). The mixture was heated at 95° C. for 0.5 hours with occasional stirring then cooled to ambient temperature. The product was extracted into dichloromethane (3×200 ml), the combined extracts were dried over magnesium sulphate, and the solvent removed in vacuo to leave 1-[1-(3,4-dichlorophenyl)-cyclobutyl]ethanone as a dark red oil (172.7 g) which was used without purification.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. temperatureheated
  4. temperatureunder reflux for a further 2.5 hours
  5. filtrationThe resulting solid was collected by filtration
  6. washwashed well with ether
  7. additionadded in portions at <20° C. to a stirred mixture of concentrated hydrochloric acid (410 ml) and water (650 ml)
  8. temperatureThe mixture was heated at 95° C. for 0.5 hours
  9. stirringwith occasional stirring
  10. temperaturethen cooled to ambient temperature
  11. extractionThe product was extracted into dichloromethane (3×200 ml)
  12. dry with materialthe combined extracts were dried over magnesium sulphate
  13. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-38cae80a86894793a74ce171ca39aa60
Source dataset
uspto-grants-1997_07
Patent number
US05652271

Linked notes

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