Hydrochloric Acid → HCID 13083375, compound

HRID 325869Notes

Reaction equation

HRID 325869 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:12]C#N)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.CBr.[Mg].Cl.CC[O:21][CH2:22][CH3:23]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:12][C:22](=[O:21])[CH3:23])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 6323Methyl BromideHCID 5462224MagnesiumHCID 13083370HCID 13083370, compound

Product 1

HCID 13083375HCID 13083375, compound

Procedure

A solution of 2-[1-(4-chlorophenyl)cyclobutyl]acetonitrile (30 g) prepared as described in Example 1 in ether (100 ml) was added to the reaction product of methyl bromide gas and magnesium turnings (5.95 g) in ether (80 ml). The mixture was heated under reflux for four hours. Ice and then concentrated hydrochloric acid (105 ml) were added and the mixture heated under reflux until all solid material had dissolved. The aqueous layer was washed with ether and the ether used for washing was combined with the ether phase of the reaction mixture. The combined ether extracts were washed with water, dried and evaporated to yield a residue which was distilled twice to yield 1-[1-(4-chlorophenyl)cyclobutyl]propan-2-one (b.p. 133°-136°/2.5 mm Hg).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for four hours
  3. temperaturethe mixture heated
  4. temperatureunder reflux until all solid material
  5. dissolutionhad dissolved
  6. washThe aqueous layer was washed with ether
  7. washfor washing
  8. washThe combined ether extracts were washed with water
  9. customdried
  10. customevaporated
  11. customto yield a residue which
  12. distillationwas distilled twice

Sources & evidence

ORD record
ord-708ff75ab5cd4f2ebdb849c83608a64d
Source dataset
uspto-grants-1984_04
Patent number
US04443449

Reaction notes

Loading…