Thionyl Chloride → 4-Phenylbenzoyl chloride

HRID 2427932Notes

Reaction equation

HRID 2427932 reaction equation
[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:4]([C:7](O)=[O:8])=[CH:3][CH:2]=1.O=S(Cl)[Cl:18]>CN(C=O)C>[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:4]([C:7]([Cl:18])=[O:8])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 66724(1,1'-Biphenyl)-4-carboxylic acid

Product 1

HCID 841514-Phenylbenzoyl chlorideYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

(1,1′-biphenyl)-4-carboxylic acid (20 g, 100.9 mmol) was refluxed for one night in 100 ml of SOCl2 in the presence of a few drops of DMF. Thionyl chloride was removed at ordinary pressure and the residue was triturated in Et2O and filtered. Yield 100% of (1,1′-biphenyl)-4-carbonyl chloride (21.9 g), white crystalline solid. m.p. 116-119° C. 1H-NMR(CHCl3) 7.41-7.73 (7H, m), 8.18 (2H, d, J=8.3 Hz). 13C-NMR(CHCl3) 128.0, 128.1, 129.5, 129.7, 132.4, 132.6, 139.6, 148.7, 168.6

Workup

  1. customThionyl chloride was removed at ordinary pressure
  2. customthe residue was triturated in Et2O
  3. filtrationfiltered

Sources & evidence

ORD record
ord-a34f74a6160947e5bfc55b506bb06753
Source dataset
uspto-grants-2011_06
Patent number
US07968748B2

Reaction notes

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