Hydrochloric Acid → 1-Butyryl-1-(4-chlorophenyl)cyclobutane

HRID 1253081Notes

Reaction equation

HRID 1253081 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]#N)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl[C:15]1C=C(C2(C#N)CCC2)C=[CH:19][C:20]=1Cl.[Mg].C(Br)CC.Cl.CC[O:36]CC>O1CCCC1>[C:12]([C:8]1([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH2:11][CH2:10][CH2:9]1)(=[O:36])[CH2:15][CH2:20][CH3:19]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether3×HCID 78401-BromopropaneHCID 986211-(4-Chlorophenyl)cyclobutanecarbonitrileHCID 5462224MagnesiumHCID 108571341-(3,4-Dichlorophenyl)-1-cyclobutane-carbonitrile

Product 1

HCID 130833671-Butyryl-1-(4-chlorophenyl)cyclobutane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(4-Chlorophenyl)-1-cyclobutanecarbonitrile (15 g) prepared in a similar manner to the 1-(3,4-dichlorophenyl)cyclobutanecarbonitrile of Example 1 in dry ether (50 ml) was added to the product of the reaction between magnesium turnings (3.18 g) and propyl bromide (15.99 g) in dry ether (50 ml). The ether was replaced by tetrahydrofuran and the mixture heated with stirring under reflux for eighteen hours. The mixture was cooled and ice and then concentrated hydrochloric acid (52 ml) added. The resulting mixture was stirred under reflux for ten hours and extracted with ether. The ether extract yielded a residue from which 1-butyryl-1-(4-chlorophenyl)cyclobutane (b.p. 106°-108°/0.3 mm Hg) was distilled.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for eighteen hours
  3. temperatureThe mixture was cooled
  4. stirringThe resulting mixture was stirred
  5. temperatureunder reflux for ten hours
  6. extractionextracted with ether
  7. extractionThe ether extract

Sources & evidence

ORD record
ord-3069d45ca5394b51835fc72a7a9a38b6
Source dataset
uspto-grants-1988_05
Patent number
US04746680

Reaction notes

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