Toluene → 4-Methoxy-4'-methylbiphenyl

HRID 1510177Notes

Reaction equation

HRID 1510177 reaction equation
C1COCC1.[C:6]1([CH3:14])[CH:11]=[CH:10][C:9]([Mg]Br)=[CH:8][CH:7]=1.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20](Cl)=[CH:19][CH:18]=1.C1(C)C=CC=CC=1>CCCCCC>[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([C:9]2[CH:10]=[CH:11][C:6]([CH3:14])=[CH:7][CH:8]=2)=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 8028TetrahydrofuranHCID 121674-ChloroanisoleHCID 178418370HCID 178418370, compound

Product 1

HCID 17047594-Methoxy-4'-methylbiphenylYield 92%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Using a THF solution of p-tolylmagnesium bromide (1.18 mL, 1.02 M, 1.2 mmol) and 1-methoxy-4-chlorobenzene (142.6 mg, 1.0 mmol) as starting materials, the reaction was performed at a scale of 1.0 mmol at 60° C. for 24 hours in the same manner as in Example 2. After performing silica gel column chromatography (toluene=15, 30 and 50% in hexane), the above compound was obtained as a white solid (0.182 g, yield=92%, purity=>99% (GC analysis)).

Workup

  1. customthe above compound was obtained as a white solid (0.182 g, yield=92%, purity=>99% (GC analysis))

Sources & evidence

ORD record
ord-6a1568cffcf0474b862dc69902c45e7a
Source dataset
uspto-grants-2012_07
Patent number
US08211820B2

Reaction notes

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