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

HRID 1194443Notes

Reaction equation

HRID 1194443 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° C./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-ac8f0af8ae2248578bd65711c25fe9ec
Source dataset
uspto-grants-1989_03
Patent number
US04814352

Reaction notes

Loading…