O-Xylene → Benzene, m-dibutyl-

HRID 485958

Reaction equation

HRID 485958 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4](Cl)[CH:3]=1.[CH2:9]([Mg]Cl)[CH2:10][CH2:11][CH3:12].C[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=1[CH3:22]>CCOCC>[CH2:9]([C:4]1[CH:3]=[CH:2][CH:7]=[CH:6][CH:5]=1)[CH2:10][CH2:11][CH3:12].[CH2:9]([C:19]1[CH:18]=[CH:17][CH:16]=[C:21]([CH2:22][CH2:3][CH2:2][CH3:7])[CH:20]=1)[CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 3

HCID 7237O-XyleneHCID 109431,3-DichlorobenzeneHCID 178418265HCID 178418265, compound

Product 2

HCID 7705ButylbenzeneHCID 204985Benzene, m-dibutyl-Yield 23%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To 2.00 g (13.60 mmole) of m-dichlorobenzene, 0.050 g (0.065 mmoles) of [NitriphosCl]PF6 in 20 mL of ether at -78° C. was added 7.0 mL (14.0 mmoles) of 2M nBuMgCl in ether. The mixture was refluxed for 2 hrs. Then, 0.841 g of o-xylene was added as an internal standard and GC analysis on Column A (70° C. (0 min), 16°/min to 220° C.) yielded 68% of 1-chloro, 3-n-butylbenzene and 23% of 1,3-di-n-butylbenzene which was confirmed by GC/MS.

Workup

  1. temperatureThe mixture was refluxed for 2 hrs

Sources & evidence

ORD record
ord-870714dc29ef48c780a280adc99835f8
Source dataset
uspto-grants-1985_08
Patent number
US04538003

Linked notes

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