Dimethylformamide → 2-Benzylbenzoyl chloride

HRID 2105178Notes

Reaction equation

HRID 2105178 reaction equation
[C:1]1([CH2:7][C:8]2[C:9]([C:14]([OH:16])=O)=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:19])=O.CN(C=O)C>C(Cl)Cl>[CH2:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]([Cl:19])=[O:16])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 11924o-Benzylbenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 126823622-Benzylbenzoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of α-phenyl-o-toluic acid (4 g, 18.28 mmol) in dry CH2Cl2 (30 mL) was added thionyl chloride (5 mL, 68.50 mmol), followed by a drop of dry DMF. The reaction mixture was refluxed for 5 hr. The solvent and excess SOCl2 was removed in vacuo to give 2-benzyl-benzoyl chloride 18 as a pale yellow oil which was used directly in next step.

Workup

  1. temperatureThe reaction mixture was refluxed for 5 hr
  2. customThe solvent and excess SOCl2 was removed in vacuo

Sources & evidence

ORD record
ord-a86dc1ea295c47b386589b5251d44cc6
Source dataset
uspto-grants-2009_08
Patent number
US07579350B2

Reaction notes

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