Benzene → HCID 19981496, compound

HRID 1461139Notes

Reaction equation

HRID 1461139 reaction equation
[C:1]1([C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([CH2:10][CH:11]=[CH2:12])[C:8]#N)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:19]([Mg]Br)[CH3:20].C1C=CC=CC=1.Cl.CC[O:32]CC>>[C:1]1([C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([CH2:10][CH:11]=[CH2:12])[C:8](=[O:32])[CH2:19][CH3:20])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 5

HCID 241BenzeneHCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 10681154HCID 10681154, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 19981496HCID 19981496, compound

Procedure

A mixture of 2,2-diphenyl-4-pentenenitrile (2.33 g), 3.0M ethylmagnesium bromide in ether (10 ml), and benzene (30 ml) was heated at reflux for 3 hours, with stirring. After cooling to room temperature, the crude intermediate was stirred with 1N hydrochloric acid for 3 hours. The hydrolysate was partitioned between water and ethyl acetate (3×). The combined extracts were washed with water and brine, dried (MgSO4), and rotary evaporated to give a crude material which was flash-chromatographed over silica gel. Elution with hexane/ethyl acetate (5:1) yielded 1.0 g of 4,4-diphenyl-6-hepten-3-one, as a colorless oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. customThe hydrolysate was partitioned between water and ethyl acetate (3×)
  4. washThe combined extracts were washed with water and brine
  5. dry with materialdried (MgSO4)
  6. customrotary evaporated
  7. customto give a crude material which
  8. customwas flash-chromatographed over silica gel
  9. washElution with hexane/ethyl acetate (5:1)

Sources & evidence

ORD record
ord-203b125c3a734479928db325430a59ad
Source dataset
uspto-grants-1991_12
Patent number
US05073629

Reaction notes

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