Sulfuric Acid → 4-Chloro-4'-ethyl-1,1'-biphenyl

HRID 2399143Notes

Reaction equation

HRID 2399143 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.S(=O)(=O)(O)O.[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

6

Reactant 4

HCID 1118Sulfuric AcidHCID 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 acid 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°-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-672e871df0114c6283912df7333c1c14
Source dataset
uspto-grants-1977_05
Patent number
US04027041

Reaction notes

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