Hydrochloric Acid → 1-(4'-Methoxy[1,1'-biphenyl]-2-yl)ethan-1-one

HRID 2101231Notes

Reaction equation

HRID 2101231 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[Al+3].[Cl-].[Cl-].[Cl-].[C:19](Cl)(=[O:21])[CH3:20].Cl>O.C(=S)=S>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=2[C:19](=[O:21])[CH3:20])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 119434-MethoxybiphenylHCID 6451240Aluminum(III) Chloride

Product 1

HCID 43213891-(4'-Methoxy[1,1'-biphenyl]-2-yl)ethan-1-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6348Carbon DisulfideSolvent

Procedure

The 4′-methoxybiphenyl (0.05 mol) and AlCl3 (0.06 mol) were dissolved in boiling CS2 (60 mL) with stirring. Acetyl chloride (0.1 mol) was added dropwise and reflux continued for 1 hour. The mixture was poured onto crushed ice (150 mL) containing water (50 mL) and HCl (50 mL). The organic phase was separated and the CS2 removed by distillation. The residue was recrystallised from aqueous isopropanol to give the title compound. δC (CDCl3, 62.9 MHz): 26.6, 55.4, 114.4, 126.6, 128.4, 129.0, 132.2, 135.3, 145.4, 159.9 and 198.0

Workup

  1. temperaturereflux
  2. additionThe mixture was poured
  3. customThe organic phase was separated
  4. customthe CS2 removed by distillation
  5. customThe residue was recrystallised from aqueous isopropanol

Sources & evidence

ORD record
ord-28c7f26a8ccf4af7a49217cf1aeb0d75
Source dataset
uspto-grants-2009_08
Patent number
US07572825B2

Reaction notes

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