Hydrochloric Acid → 1-Butyryl-1-(3,4-dichlorophenyl)cyclobutane

HRID 1382459Notes

Reaction equation

HRID 1382459 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:13]#N)[CH2:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH2:15]([Mg]Br)[CH2:16][CH3:17].C(Br)CC.[Mg].Cl.CC[O:28]CC>O.C1(C)C=CC=CC=1>[C:13]([C:9]1([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[CH2:12][CH2:11][CH2:10]1)(=[O:28])[CH2:15][CH2:16][CH3:17]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether3×HCID 78401-BromopropaneHCID 5462224MagnesiumHCID 108571341-(3,4-Dichlorophenyl)-1-cyclobutane-carbonitrileHCID 178455851HCID 178455851, compound

Product 1

HCID 130833791-Butyryl-1-(3,4-dichlorophenyl)cyclobutane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of 1-(3,4-dichlorophenyl)-1-cyclobutanecarbonitrile prepared as described in Example 1 (35.2 g) in ether (100 ml) was added to a solution of propyl magnesium bromide prepared by the reaction of propyl bromide (32 g) with magnesium turnings (6.36 g) in ether (100 ml). The ether was replaced by dry toluene and the mixture heated under reflux for one hour. Water (200 ml) and then concentrated hydrochloric acid (120 ml) were added and the mixture heated under reflux for one hour. The reaction mixture was extracted with ether and after washing and drying the extract yielded a residue from which 1-butyryl-1-(3,4-dichlorophenyl)cyclobutane (b.p. 120°-128° C. at 0.25 mm) was distilled.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for one hour
  3. temperaturethe mixture heated
  4. temperatureunder reflux for one hour
  5. extractionThe reaction mixture was extracted with ether
  6. washafter washing
  7. customdrying the extract

Sources & evidence

ORD record
ord-6b443751068d420b9a55423f71ad019b
Source dataset
uspto-grants-1989_02
Patent number
US04806570

Reaction notes

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