Hydrochloric Acid → 1-[1-(3,4-Dichlorophenyl)cyclobutyl]-4-methoxybutanone

HRID 635356Notes

Reaction equation

HRID 635356 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].[CH3:15][O:16][CH2:17][CH2:18][CH2:19][Mg]Br.BrCCC[O:26]C.[Mg].Cl>CCOCC>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:13][C:19](=[O:26])[CH2:18][CH2:17][O:16][CH3:15])[CH2:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 5245511-Bromo-3-methoxypropaneHCID 5462224MagnesiumHCID 108571341-(3,4-Dichlorophenyl)-1-cyclobutane-carbonitrileHCID 178495108HCID 178495108, compound

Product 1

HCID 571209991-[1-(3,4-Dichlorophenyl)cyclobutyl]-4-methoxybutanone

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 1-(3,4-dichlorophenyl)cyclobutanecarbonitrile (15 g) in ether (50 ml) was added dropwise to a stirred solution of 3-methoxypropylmagnesium bromide [prepared in the usual manner from 1-bromo-3-methoxypropane (15.3 g) and magnesium (2.4 g)] in ether (55 ml), then the mixture was stirred at reflux temperature for 2.5 hours, cooled to ambient temperature, and added to a mixture of crushed ice (100 g) and concentrated hydrochloric acid (80 ml). The resulting mixture was heated at 95° C. with occasional stirring for 1.5 hours, then it was allowed to stand at ambient temperature for 48 hours. The product was extracted into ether (3×100 ml), and the combined extracts were washed with water (100 ml), saturated aqueous sodium hydrogen carbonate solution (100 ml) and water (100 ml), dried (MgSO4), and the solvent was removed in vacua. The residue was distilled to give 1-[1-(3,4-dichlorophenyl)cyclobutyl]-4-methoxybutanone as a pale yellow oil (16.4 g), b.p. 138-147° C./0.5 mbar.

Workup

  1. temperatureat reflux temperature for 2.5 hours
  2. temperatureThe resulting mixture was heated at 95° C.
  3. stirringwith occasional stirring for 1.5 hours
  4. extractionThe product was extracted into ether (3×100 ml)
  5. washthe combined extracts were washed with water (100 ml), saturated aqueous sodium hydrogen carbonate solution (100 ml) and water (100 ml)
  6. dry with materialdried (MgSO4)
  7. customthe solvent was removed in vacua
  8. distillationThe residue was distilled

Sources & evidence

ORD record
ord-789ab128a54141bf9c211602827f9da5
Source dataset
uspto-grants-2001_02
Patent number
US06187802B1

Reaction notes

Loading…