Hydrochloric Acid → 2-(p-Biphenylyl)-2-penten-4-one

HRID 67133Notes

Reaction equation

HRID 67133 reaction equation
[C:1]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7](O)([CH:9]=[C:10]=[CH2:11])[CH3:8].Cl.C[OH:21]>>[C:1]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7](=[CH:9][C:10](=[O:21])[CH3:11])[CH3:8]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 867348952-(p-Biphenylyl)-3,4-pentadien-2-ol

Product 1

HCID 545652342-(p-Biphenylyl)-2-penten-4-one

Procedure

To a solution of 10 g. of 2-(p-biphenylyl)-3,4-pentadien-2-ol in 200 ml. of anhydrous methanol is added 3 ml. of concentrated hydrochloric acid (12 N). The resulting mixture is stirred at room temperaure for 3 hours and then in an ice bath for 2 hours. Solids formed are filtered off and recrystallized from pentane to obtain 2-(p-biphenylyl)-2-penten-4-one, m.p. 130°-133° C. 2-(p-(biphenylyl)-4-chloro-2,4-pentadiene, byproduct, remains in the mother liquor.

Workup

  1. waitin an ice bath for 2 hours
  2. customSolids formed
  3. filtrationare filtered off
  4. customrecrystallized from pentane

Sources & evidence

ORD record
ord-ff9d386997e44cd282bcd919d45b9317
Source dataset
uspto-grants-1982_08
Patent number
US04344966

Reaction notes

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