1-octoxyoctane

Conditions: temp:100.01; pressure:0.00; stir:

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

Procedure: The use of quaternary salt catalysts in the production of symmetrical ethers is also known. A. W. Herriott and D. Picker (Tet. Lett. 44, p. 4,521 (1972)) teach that the reaction of 1-bromooctane with 2N sodium hydroxide in the presence of a quaternary ammonium salt catalyst produces di-n-octyl ether in 75% yield. R. D. Gordon (U.S. Pat. No. 3,824,295) also teaches that the reaction of an alkyl halide, sulfate or sulfonate with aqueous caustic in the presence of a quaternary salt catalyst produces a symmetrical ether.

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

Procedure: Control Reaction using NAFION 117: From the combination of 0.5 mL 1-octanol (3.17 mmol) and 0.314 g NAFION 117 (0.28 meq (0.89 meq/g)) in 3.0 mL toluene (1.1 M) as solvent was obtained 12.4 mg n-octyl ether (3% isolated yield) upon purification of the crude product (GC ratio of 90:10 (octanol:octyl ether)) by bulb-to-bulb distillation (bp 130° C./3 mm Hg (air bath temp)). Control Reaction

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

Procedure: Control Reaction using NAFION 117: From the combination of 0.5 mL 1-octanol (3.17 mmol) and 0.314 g NAFION 117 (0.28 meq (0.89 meq/g)) in 3.0 mL toluene (1.1 M) as solvent was obtained 12.4 mg n-octyl ether (3% isolated yield) upon purification of the crude product (GC ratio of 90:10 (octanol:octyl ether)) by bulb-to-bulb distillation (bp 130° C./3 mm Hg (air bath temp)). Control Reaction

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

Procedure: 206 kg (1581.8 moles) of n-octanol were heated to 190°-210° C. together with 2.94 kg of sulfosuccinic acid (70% by weight). The water of reaction formed was distilled off. After 7 hours, 10.3 g of 50% by weight sodium hydroxide were added to the cooled reaction mixture for neutralization, after which the crude product was washed until neutral and then distilled. formed was distilled off 10.3 g of 50% by weight sodium hydroxide were added to the cooled reaction mixture for neutralization after which the crude product was washed until neutral and then distilled

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

Procedure: Control Reaction using NAFION 117: From the combination of 0.5 mL 1-octanol (3.17 mmol) and 0.314 g NAFION 117 (0.28 meq (0.89 meq/g)) in 3.0 mL toluene (1.1 M) as solvent was obtained 12.4 mg n-octyl ether (3% isolated yield) upon purification of the crude product (GC ratio of 90:10 (octanol:octyl ether)) by bulb-to-bulb distillation (bp 130° C./3 mm Hg (air bath temp)). Control Reaction

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

Procedure: Control Reaction using NAFION 117: From the combination of 0.5 mL 1-octanol (3.17 mmol) and 0.314 g NAFION 117 (0.28 meq (0.89 meq/g)) in 3.0 mL toluene (1.1 M) as solvent was obtained 12.4 mg n-octyl ether (3% isolated yield) upon purification of the crude product (GC ratio of 90:10 (octanol:octyl ether)) by bulb-to-bulb distillation (bp 130° C./3 mm Hg (air bath temp)). Control Reaction

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

Procedure: The use of quaternary salt catalysts in the production of symmetrical ethers is also known. A. W. Herriott and D. Picker (Tet. Lett. 44, p. 4,521 (1972)) teach that the reaction of 1-bromooctane with 2N sodium hydroxide in the presence of a quaternary ammonium salt catalyst produces di-n-octyl ether in 75% yield. R. D. Gordon (U.S. Pat. No. 3,824,295) also teaches that the reaction of an alkyl halide, sulfate or sulfonate with aqueous caustic in the presence of a quaternary salt catalyst produces a symmetrical ether.

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

Procedure: Control Reaction using NAFION 117: From the combination of 0.5 mL 1-octanol (3.17 mmol) and 0.314 g NAFION 117 (0.28 meq (0.89 meq/g)) in 3.0 mL toluene (1.1 M) as solvent was obtained 12.4 mg n-octyl ether (3% isolated yield) upon purification of the crude product (GC ratio of 90:10 (octanol:octyl ether)) by bulb-to-bulb distillation (bp 130° C./3 mm Hg (air bath temp)). Control Reaction