Toluene → Methyl 3-(4-methylphenyl)benzoate

HRID 1418614Notes

Reaction equation

HRID 1418614 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[C:12]1([CH3:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>IC1C=CC(C)=CC=1.[Cu]>[CH3:18][C:12]1[CH:17]=[CH:16][C:15]([C:2]2[CH:11]=[CH:10][CH:9]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:3]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 1140TolueneHCID 69258Methyl 3-iodobenzoate

Product 1

HCID 1394187Methyl 3-(4-methylphenyl)benzoateYield 29%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 122074-IodotolueneSolvent

Procedure

To a mixture of methyl 3-iodobenzoate (26.1 g) in 4-iodotoluene (21.9 g) was added copper powder (31.8 g) gradually at 180°-190° C. The mixture was then stirred for 6 hours at 200°-210° C. The reaction mixture was cooled to room temperature, to which was added toluene. Insoluble materials were filtered off, and the filtrate was concentrated to dryness. The residue was purified by column chromatography on silica gel to afford the title compound as a colorless oil (6.61 g, 29%).

Workup

  1. filtrationInsoluble materials were filtered off
  2. concentrationthe filtrate was concentrated to dryness
  3. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-f1269498dff44f3db0635554244155d0
Source dataset
uspto-grants-1999_03
Patent number
US05883111

Reaction notes

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