Toluene → Methyl 3-(4-methylphenyl)benzoate

HRID 5237

Reaction equation

HRID 5237 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-2fe8b08f64c844be852d3e2cfd2c0a0e
Source dataset
uspto-grants-1993_09
Patent number
US05243054

Linked notes

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