2-hexoxyphenol

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

Procedure: To 350 mL of dehydrated methylene chloride, 12.8 g (66 mmol) of 2-hexyloxyphenol, 23.3 g (73 mmol) of 16-bromohexadecane-1-ol, and 20.0 g (99 mmol) of tri-n-butylphosphine were added. The resulting mixture was cooled with ice under argon. After 25.0 g (99 mmol) of 1,1′-(azodicarbonyl)dipiperidine was added bit by bit while stirring the mixture, 150 mL of methylene chloride was added. Under argon, the mixture was stirred at ambient temperature for 30 minutes and was refluxed for 6 hours. After being cooled, the reaction solution was put into 100 mL of hexane and was filtered. The filtered liquid was purified by silica-gel column chromatography. As a result, 26.5 g of a transparent liquid was obtained. The resulting mixture was cooled with ice under argon was added was refluxed for 6 hours After being cooled was filtered The filtered liquid was purified by silica-gel column chromatography

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

Procedure: To 350 mL of dehydrated methylene chloride, 12.8 g (66 mmol) of 2-hexyloxyphenol, 23.3 g (73 mmol) of 16-bromohexadecane-1-ol, and 20.0 g (99 mmol) of tri-n-butylphosphine were added. The resulting mixture was cooled with ice under argon. After 25.0 g (99 mmol) of 1,1′-(azodicarbonyl)dipiperidine was added bit by bit while stirring the mixture, 150 mL of methylene chloride was added. Under argon, the mixture was stirred at ambient temperature for 30 minutes and was refluxed for 6 hours. After being cooled, the reaction solution was put into 100 mL of hexane and was filtered. The filtered liquid was purified by silica-gel column chromatography. As a result, 26.5 g of a transparent liquid was obtained. The resulting mixture was cooled with ice under argon was added was refluxed for 6 hours After being cooled was filtered The filtered liquid was purified by silica-gel column chromatography

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

Procedure: A mixture of 740 mL of methyl ethyl ketone, 120 g (1.09 mol) of catechol, 178 g (1.09 mmol) of 1-bromohexane, and 211 g (1.53 mol, 1.4 eq.) of potassium carbonate was refluxed for 25 hours. After being cooled, the mixture was filtered and the solvent was evaporated. The residue of 202 g was purified by silica-gel column chromatography and was then distilled. As a result, 101 g of a transparent liquid was obtained. was refluxed for 25 hours After being cooled the mixture was filtered the solvent was evaporated The residue of 202 g was purified by silica-gel column chromatography was then distilled

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

Procedure: A mixture of 740 mL of methyl ethyl ketone, 120 g (1.09 mol) of catechol, 178 g (1.09 mmol) of 1-bromohexane, and 211 g (1.53 mol, 1.4 eq.) of potassium carbonate was refluxed for 25 hours. After being cooled, the mixture was filtered and the solvent was evaporated. The residue of 202 g was purified by silica-gel column chromatography and was then distilled. As a result, 101 g of a transparent liquid was obtained. was refluxed for 25 hours After being cooled the mixture was filtered the solvent was evaporated The residue of 202 g was purified by silica-gel column chromatography was then distilled

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

Procedure: Acetyl chloride (2.4 g, 30.1 mmol) was added dropwise to vigorously stirred mixture of 2-hexyloxyphenol (5.0 g, 25.8 mmol) and pyridine (5 ml) in dichloromethane (50 ml). The mixture was stirred for 1 hour and poured onto water. The organic layer was separated, dried (MgSO4), concentrated to give crude product which was purified by column chromatography on silica gel using dichloromethane petroleum spirit (1:3) as eluent to give title compound as a colourless oil (5.78 g, 95%). Found: C, 71.00; H, 8.35. C14H20O3 requires C, 71.19; H, 8.47. δH (CHCl3) 7.21-7.15 (m, 1H, ArH), 7.05-7.01 (m, 1H, ArH), 6.97-6.89 (m, 2H, ArH), 3.97 (t, J 6.5, 2H, OCH2), 2.30 (s, 3H, COCH3), 1.78-1.71 (m, 2H, ArOCH2CH2), 1.57-1.30 (m, 6H, CH2), 0.90 (t, J 6.9, 3H, CH2CH3). MS (FAB), 236 (M+, 53%), 194 (100%), 153 (27%), 110 (34%), 85 (7%), 55 (7%). poured onto water The organic layer was separated dried (MgSO4) concentrated to give crude product which was purified by column chromatography on silica gel

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

Procedure: Catechol (35.0 g, 0.32 mol), potassium carbonate (109.0 g, 0.79 mol) and 1-bromohexane (52.5 g, 0.32 mol) were added to ethanol (300 ml) and heated under reflux for 48 h. After cooling, dichloromethane (300 ml) was added and the solid residues removed by filtration. The solvents were then removed in vacuo and the crude product was purified by column chromatography on silica gel to give title compound (17.9 g, 29%) as a colourless liquid. Found: C, 73.90; H, 9.20. C12H18O2 requires C, 74.19; H, 9.34. δH (CHCl3) 6.95-6.83 (m, 4H, ArH), 5.66 (s, 1H, OH), 4.04 (t, J 7, 2H, ArOCH2), 1.89-1.79 (m, 2H, ArOCH2CH), 1.55-1.35 (m, 6H, CH2), 0.95 (t, J 7, 3H, CH2CH3). MS (FAB), 194 (M+, 100%), 110 (45%), 95 (7%), 83 (12%), 69 (9%), 55 (18%). heated under reflux for 48 h After cooling the solid residues removed by filtration The solvents were then removed in vacuo the crude product was purified by column chromatography on silica gel

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

Procedure: 12.8 g (66 mmol) of 2-hexyloxyphenol, 23.3 g (73 mmol) of 16-bromohexadecan-1-ol and 20.0 g (99 mmol) of tri-n-butylphosphine were added to 350 mL of dehydrated methylene chloride followed by cooling with ice in the presence of argon. After adding 25.0 g (99 mmol) of 1,1′-(azodicarbonyl) dipiperidine a little at a time while stirring, 150 mL of methylene chloride were added. After stirring for 30 minutes at room temperature in the presence of argon, the reaction solution was refluxed for 6 hours. After cooling, the reaction solution was dropped into 100 mL of hexane and filtered. The filtrate was concentrated and purified by silica gel column chromatography to obtain 26.5 g of a clear liquid. by cooling with ice in the presence of argon After stirring for 30 minutes at room temperature in the presence of argon the reaction solution was refluxed for 6 hours After cooling filtered The filtrate was concentrated purified by silica gel column chromatography

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

Procedure: A mixture consisting of 740 mL of methyl ethyl ketone, 120 g (1.09 mol) of catechol, 178 g (1.09 mmol) of 1-bromohexane and 211 g (1.53 mol, 1.4 eq.) of potassium carbonate was refluxed for 25 hours. After cooling, the mixture was filtered followed by distilling off the solvent. 202 g of residue was purified by silica gel column chromatography followed by distillation to obtain 101 g of a clear liquid. was refluxed for 25 hours After cooling the mixture was filtered by distilling off the solvent 202 g of residue was purified by silica gel column chromatography followed by distillation