4-acetyl-4'-chlorobiphenyl → 4-Chloro-4'-ethyl-1,1'-biphenyl

HRID 1283631Notes

Reaction equation

HRID 1283631 reaction equation
ClC1C=CC=CC=1C1C=CC(C(=O)C)=CC=1.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][C:27]([C:30](=O)[CH3:31])=[CH:26][CH:25]=2)=[CH:20][CH:19]=1.[H][H]>C1C=CC=CC=1>[CH2:30]([C:27]1[CH:28]=[CH:29][C:24]([C:21]2[CH:22]=[CH:23][C:18]([Cl:17])=[CH:19][CH:20]=2)=[CH:25][CH:26]=1)[CH3:31]

Participants

5

Reactant 3

HCID 5925694-acetyl-4'-chlorobiphenylHCID 6120001-(2′-Chloro[1,1′-biphenyl]-4-yl)ethanoneHCID 178418361HCID 178418361, compound

Product 1

HCID 132706404-Chloro-4'-ethyl-1,1'-biphenyl

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The procedure of Example 3 was repeated, except that the 4'-(2-chlorophenyl)acetophenone was replaced with an equal amount of 4'-(4-chlorophenyl)acetophenone, the amount of benzene employed was increased to 200 ml, and the amount of sulfuric was reduced to 5 drops. After seven hours, hydrogen pressure had dropped to 35.5 psig. Evaporation of the benzene left a solid which, according to nuclear magnetic resonance analysis, contained only about 67 percent of the desired ethylbenzene. Consequently, the solid was subjected to the hydrogenation procedure again, using 200 ml of benzene, 2 g of catalyst, and 1 ml of concentrated sulfuric acid. The solid obtained upon evaporation of the benzene was recrystallized from hexane, giving 1-ethyl-4-(4-chlorophenyl)benzene, mp 103°-127 104°. The following elemental analysis was obtained:

Workup

  1. customEvaporation of the benzene
  2. waitleft a solid which
  3. customThe solid obtained upon evaporation of the benzene
  4. customwas recrystallized from hexane

Sources & evidence

ORD record
ord-d84cbbcf2e2c418f83465ca03108086d
Source dataset
uspto-grants-1976_08
Patent number
US03975542

Reaction notes

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