Chlorobenzene → 1,2-Bis(4-chlorophenyl)ethanone

HRID 2205122Notes

Reaction equation

HRID 2205122 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:9](=[O:11])[CH2:8][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 7964ChlorobenzeneHCID 15880(4-Chlorophenyl)acetic acid

Product 1

HCID 5873181,2-Bis(4-chlorophenyl)ethanoneYield 59.8%

Procedure

The diaryl product was obtained using the same synthetic methods as shown in Example 25, step 5, using 2-(4-chlorophenyl)acetic acid (5 g, 29.2 mmol) and chlorobenzene (10.31 g, 91.2 mmol, 2.85 equiv) as reactants. The reaction was quenched by the addition of water/ice. The residue was dissolved in 3% HCl, extracted with 3×20 mL of dichloromethane, and the organic layers combined and concentrated under vacuum. Purification via silica gel column (ethyl acetate/petroleum ether (1:100)) yielded 4.63 g (54%) of 1,2-bis(4-chlorophenyl)ethanone as a white solid.

Workup

  1. customThe reaction was quenched by the addition of water/ice
  2. dissolutionThe residue was dissolved in 3% HCl
  3. extractionextracted with 3×20 mL of dichloromethane
  4. concentrationconcentrated under vacuum
  5. customPurification via silica gel column (ethyl acetate/petroleum ether (1:100))

Sources & evidence

ORD record
ord-d0c91df083e94a05b28cb289983203bd
Source dataset
uspto-grants-2016_06
Patent number
US09370522B2

Reaction notes

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