Toluene → Methyl 3-(4-methylphenyl)benzoate

HRID 1080824Notes

Reaction equation

HRID 1080824 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

Conditions

Temperature
205 °C

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. temperatureThe reaction mixture was cooled to room temperature, to which
  2. filtrationInsoluble materials were filtered off
  3. concentrationthe filtrate was concentrated to dryness
  4. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-bb80eaa795524d0f9ad16f75f29be36e
Source dataset
uspto-grants-1996_12
Patent number
US05583141

Reaction notes

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