octylbenzene

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Aluminum chloride (22.6 g) is suspended in dichloroethane (500 ml) and octylbenzene (16) (21.5 g) is added at room temperature. To the mixture is added acetyl chloride (8.87 g) under ice-cooling. The mixture is stirred at room temperature overnight. The reaction mixture is poured into ice water and extracted with ether. The organic layer is washed with brine and dried over sodium sulfate. The solvent is evaporated to give 4′-octylacetophenone (18′) as a colorless oil. cooling extracted with ether The organic layer is washed with brine dried over sodium sulfate The solvent is evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Phenylglyoxal monohydrate (608 mg, 4 mM) and n-octylbenzene (1.77 ml, 8 mM) were dissolved in dichloroethane (8 ml), titanium tetrachloride (0.66 ml, 6 mM) was added, and reacted at room temperature for 30 minutes. Using the same procedure as in Example 1, 4'-n-octylbenzoin was obtained as crystal (810.0 mg, 62.6% yield). reacted at room temperature for 30 minutes

Conditions: temp:2.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: AlCl3 (12.0 g, 89.0 mmol) was added to 15 ml of methylene chloride and cooled to 0-5° C., following by addition of 3-nitropropanoyl chloride (11 g, 80 mmol). Octylbenzene (17.10 g, 89.0 mmol) in 40 ml of CH2Cl2 was dropwise added and the solution was stirred at room temperature under TLC monitoring. After reaction completion, the mixture was poured onto ice, acidified by addition of 2 M HCl to pH 2, and extracted with CH2Cl2. The combined organic extracts were washed again with 2 M HCl and water, dried over Na2SO4, filtered, and the solvent was removed under reduced pressure to yield a solid that was recrystallized (hexanes) to give 3-nitro-1-phenylpropan-1-one (76%); mp 59-62° C., ESIMS 292 [M+H]+. After reaction completion the mixture was poured onto ice extracted with CH2Cl2 The combined organic extracts were washed again with 2 M HCl and water dried over Na2SO4 filtered the solvent was removed under reduced pressure to yield a solid that was recrystallized (hexanes)

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Nickel(II) bis-triflimide (0.06 g, 0.1 mmol) was dissolved in [bmim][NTf2] (1.0 g) in a round-bottomed flask equipped with a magnetic stirrer and reflux condenser. Benzene (3.90 g, 50 mmol) and oct-1-ene (1.12 g, 10 mmol) were added. The mixture was heated under reflux for 18 hours and was analysed by gas chromatographic analysis as in previous examples. The oct-1-ene peak disappeared and three isomers of octylbenzene were formed (70%, 20:26:54 2- to 3- to 4-isomer ratio) as well as octene dimer (30%). The less dense product phase was decanted from the ionic/catalyst phase and purified by Kugelrohr distillation. The ionic liquid and catalyst were prepared for reuse by heating at 60° C. under vacuum for 1 hour. The ionic liquid and catalyst were used for further reactions of benzene with oct-1-ene without loss of activity. This is an alkylation of benzene with an alkene using a metal bis-triflimide catalyst. Benzene and oct-1-ene react in the presence of 1% nickel(II) bis-triflimide in [bmim][NTf2] to form three isomers of octyl benzene and a small amount of hexadecene (unknown isomeric distribution). This is shown below: The Alkylation of Benzene with oct-1-ene. The less dense product phase was decanted from the ionic/catalyst phase purified by Kugelrohr distillation The ionic liquid and catalyst were prepared for reuse

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Nickel(II) bis-triflimide (0.06 g, 0.1 mmol) was dissolved in [bmim][NTf2] (1.0 g) in a round-bottomed flask equipped with a magnetic stirrer and reflux condenser. Benzene (3.90 g, 50 mmol) and oct-1-ene (1.12 g, 10 mmol) were added. The mixture was heated under reflux for 18 hours and was analysed by gas chromatographic analysis as in previous examples. The oct-1-ene peak disappeared and three isomers of octylbenzene were formed (70%, 20:26:54 2- to 3- to 4-isomer ratio) as well as octene dimer (30%). The less dense product phase was decanted from the ionic/catalyst phase and purified by Kugelrohr distillation. The ionic liquid and catalyst were prepared for reuse by heating at 60° C. under vacuum for 1 hour. The ionic liquid and catalyst were used for further reactions of benzene with oct-1-ene without loss of activity. This is an alkylation of benzene with an alkene using a metal bis-triflimide catalyst. Benzene and oct-1-ene react in the presence of 1% nickel(II) bis-triflimide in [bmim][NTf2] to form three isomers of octyl benzene and a small amount of hexadecene (unknown isomeric distribution). This is shown below: The Alkylation of Benzene with oct-1-ene. The less dense product phase was decanted from the ionic/catalyst phase purified by Kugelrohr distillation The ionic liquid and catalyst were prepared for reuse

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Nickel(II) bis-triflimide (0.06 g, 0.1 mmol) was dissolved in [bmim][NTf2] (1.0 g) in a round-bottomed flask equipped with a magnetic stirrer and reflux condenser. Benzene (3.90 g, 50 mmol) and oct-1-ene (1.12 g, 10 mmol) were added. The mixture was heated under reflux for 18 hours and was analysed by gas chromatographic analysis as in previous examples. The oct-1-ene peak disappeared and three isomers of octylbenzene were formed (70%, 20:26:54 2- to 3- to 4-isomer ratio) as well as octene dimer (30%). The less dense product phase was decanted from the ionic/catalyst phase and purified by Kugelrohr distillation. The ionic liquid and catalyst were prepared for reuse by heating at 60° C. under vacuum for 1 hour. The ionic liquid and catalyst were used for further reactions of benzene with oct-1-ene without loss of activity. This is an alkylation of benzene with an alkene using a metal bis-triflimide catalyst. Benzene and oct-1-ene react in the presence of 1% nickel(II) bis-triflimide in [bmim][NTf2] to form three isomers of octyl benzene and a small amount of hexadecene (unknown isomeric distribution). This is shown below: The Alkylation of Benzene with oct-1-ene. equipped with a magnetic stirrer reflux condenser The mixture was heated under reflux for 18 hours

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of n-octylbenzene (1.2 g; 6.3 mmol) hexamethylenetetramine (0.97 g; 6.93 mmol) in trifluoroacetic acid (TFA) was refluxed for 4 h, cooled to room temperature and evaporated to dryness under reduced pressure. The residue was neutralized with 5% NaHCO3 and extracted with diethyl ether (Et2O) (3×5 ml). The combined organic phase was washed with H2O, brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated under reduced pressure and the residue was purified by FCC (SiO2, hexane) to give the title compound (0.4 g; 29%) as a colourless oil and starting n-octylbenzene (0.8 g; 67%). 1H-NMR (CDCl3) 9.96 (s, 1H); 7.77 (d, 2H, J=8.1 Hz); 7.31 (d, 2H, J=8.1 Hz); 2.67 (t, 2H, J=7.9 Hz); 1.6 (m, 2H); 1.26 (m, 10H); 0.86 (t, 3H, J=6.9 Hz); was refluxed for 4 h evaporated to dryness under reduced pressure extracted with diethyl ether (Et2O) (3×5 ml) The combined organic phase was washed with H2O, brine dried over anhydrous MgSO4 filtered The filtrate was evaporated under reduced pressure the residue was purified by FCC (SiO2, hexane)