Sulfuric Acid → 2-Chloro-4'-ethyl-1,1'-biphenyl

HRID 2399142Notes

Reaction equation

HRID 2399142 reaction equation
C(C1C=CC(C2C=CC=CC=2F)=CC=1)#C.[Cl:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]1[CH:28]=[CH:27][C:26]([C:29](=O)[CH3:30])=[CH:25][CH:24]=1.S(=O)(=O)(O)O>C1C=CC=CC=1>[CH2:29]([C:26]1[CH:27]=[CH:28][C:23]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[Cl:16])=[CH:24][CH:25]=1)[CH3:30]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 42040FluretofeneHCID 6120001-(2′-Chloro[1,1′-biphenyl]-4-yl)ethanone

Product 1

HCID 132706352-Chloro-4'-ethyl-1,1'-biphenylYield 64.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The procedure of Example 1 was repeated, except that the 1-ethynyl-4-(2-fluorophenyl)benzene was replaced with 23.1 g of 4'-(2-chlorophenyl)acetophenone, the amount of benzene was increased to 150 ml, the amount of catalyst was increased to 3 g, the amount of sulfuric acid was increased to 2 ml, and the reduction was allowed to proceed for 13 hours. Evaporation of the benzene left a residue which was vacuum distilled to give 14 g of 1-ethyl-4-(2-chlorophenyl)benzene, bp 110°-112°/0.4 mm. The following elemental anaylsis was obtained:

Workup

  1. temperaturethe amount of catalyst was increased to 3 g
  2. customEvaporation of the benzene
  3. waitleft a residue which
  4. distillationdistilled

Sources & evidence

ORD record
ord-bc9670d4e58846b1adcf92914f1217ce
Source dataset
uspto-grants-1977_05
Patent number
US04027041

Reaction notes

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