1-(2-bromoethoxy)butane

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

Procedure: To a 1 l three-neck flask were added 70 g of sodium salt of p-hydroxybenzoic acid ##STR4## and 200 ml of N,N-dimethylformamide, and the contents were heated under reflux. To the heated contents, 50 g of β-n-butoxyethyl bromide was dropped over a period of 30 minutes and heating was continued under reflux for further 8 hours. After cooling with water, 300 ml of water and 200 ml of toluene were added to the contents and after shaking, the resulting organic layer was separated, washed with 4 N hydrochloric acid and then with a 20% aqueous solution of sodium hydroxide. After distilling off toluene and heating the remaing material together with 200 ml of a 20% aqueous solution of sodium hydroxide for 3 hours, the resulting material was neutralized with hydrochloric acid to precipitate the objective material. After washing with water, the objective material was recrystallized from ethanol to obtain 55 g of p-(β-n-butoxy)ethoxybenzoic acid. The melting point of this material was 114.5°-115° C. and the values of the elemental analysis thereof showed a good agreement with the calculated values as seen below. under reflux heating under reflux for further 8 hours were added to the contents the resulting organic layer was separated washed with 4 N hydrochloric acid After distilling off toluene heating the remaing material together with 200 ml of a 20% aqueous solution of sodium hydroxide for 3 hours to precipitate the objective material After washing with water the objective material was recrystallized from ethanol

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

Procedure: One gram (5.5 millimoles) of 1-bromo-2-butoxyethane was combined with 5.5 grams (30 millimoles) of 4,4'-dihydroxybiphenyl in 75 mls. of acetonitrile. To the reaction mixture were added 8.3 grams (60 millimoles) of finely ground potassium carbonate. Stirring was begun and the reaction mixture was brought to reflux and maintained for 48 hours. The reaction product was filtered, washed with acetonitrile and evaporated for removal of solvent. The product was passed through a silica gel chromatographic column using dichloromethane eluent, for recovery of 0.25 gram (20% yield) of a biphenol ether compound having the following formula confirmed by TLC, IR and mass spectral analyses: ##STR26## to reflux maintained for 48 hours The reaction product was filtered washed with acetonitrile evaporated for removal of solvent

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

Procedure: Nine grams (0.05 mole) of 1-bromo-2-butoxy-ethane and 6.1 grams (0.05 mole) of 4-hydroxybenzaldehyde were dissolved in 75 mls. of acetonitrile. Into the mixture were added 13.8 grams (0.1 mole) of finely ground potassium carbonate and the resulting reaction mixture was stirred under reflux for ten hours. The reaction mixture was allowed to cool, was filtered, washed with acetonitrile and evaporated to an amber oily product. The product was passed through a silica gel chromatographic column for recovery of a colorless oil (64% yield) having the following structure: ##STR20## the resulting reaction mixture under reflux for ten hours to cool was filtered washed with acetonitrile evaporated to an amber oily product

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

Procedure: Nine grams (0.05 mole) of 1-bromo-2-butoxy-ethane and 6.1 grams (0.05 mole) of 4-hydroxybenzaldehyde were dissolved in 75 mls. of acetonitrile. Into the mixture were added 13.8 grams (0.1 mole) of finely ground potassium carbonate and the resulting reaction mixture was stirred under reflux for ten hours. The reaction mixture was allowed to cool, was filtered, washed with acetonitrile and evaporated to an amber oily product. The product was passed through a silica gel chromatographic column for recovery of a colorless oil (64% yield) having the following structure: ##STR20## the resulting reaction mixture under reflux for ten hours to cool was filtered washed with acetonitrile evaporated to an amber oily product

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

Procedure: To a 1 l three-neck flask were added 70 g of sodium salt of p-hydroxybenzoic acid ##STR4## and 200 ml of N,N-dimethylformamide, and the contents were heated under reflux. To the heated contents, 50 g of β-n-butoxyethyl bromide was dropped over a period of 30 minutes and heating was continued under reflux for further 8 hours. After cooling with water, 300 ml of water and 200 ml of toluene were added to the contents and after shaking, the resulting organic layer was separated, washed with 4 N hydrochloric acid and then with a 20% aqueous solution of sodium hydroxide. After distilling off toluene and heating the remaing material together with 200 ml of a 20% aqueous solution of sodium hydroxide for 3 hours, the resulting material was neutralized with hydrochloric acid to precipitate the objective material. After washing with water, the objective material was recrystallized from ethanol to obtain 55 g of p-(β-n-butoxy)ethoxybenzoic acid. The melting point of this material was 114.5°-115° C. and the values of the elemental analysis thereof showed a good agreement with the calculated values as seen below. under reflux heating under reflux for further 8 hours were added to the contents the resulting organic layer was separated washed with 4 N hydrochloric acid After distilling off toluene heating the remaing material together with 200 ml of a 20% aqueous solution of sodium hydroxide for 3 hours to precipitate the objective material After washing with water the objective material was recrystallized from ethanol

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6.1 g of 2-thiopheneethanol was cooled to 0° C., and to this, a suspension formed by adding 2.8 g of sodium hydride (60% in oil) to 50 ml of tetrahydrofuran was added dropwise. The solution was stirred at 0° C. for 20 minutes under a nitrogen atmosphere, and to this, 8.2 g of 1-(2-bromo-ethoxy)-butane was added dropwise. Thereafter, the solution was heated to 90° C. and stirred for 9 hours. 100 ml of water and 100 ml of hexane were added to the reaction solution to separate the organic layer. The organic layer was washed with 300 ml of water and then dried over anhydrous magnesium sulfate. The resulting solution was concentrated by a rotary evaporator and purified by a column chromatography (filler: silica gel, eluent: hexane/dichloromethane) to obtain 3.5 g of 2-[2-(2-butoxy-ethoxy)ethyl]-thiophene. to this, a suspension formed was added dropwise Thereafter, the solution was heated to 90° C. stirred for 9 hours to separate the organic layer The organic layer was washed with 300 ml of water dried over anhydrous magnesium sulfate The resulting solution was concentrated by a rotary evaporator purified by a column chromatography (filler: silica gel, eluent: hexane/dichloromethane)

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

Procedure: One gram (5.5 millimoles) of 1-bromo-2-butoxyethane was combined with 5.5 grams (30 millimoles) of 4,4'-dihydroxybiphenyl in 75 mls. of acetonitrile. To the reaction mixture were added 8.3 grams (60 millimoles) of finely ground potassium carbonate. Stirring was begun and the reaction mixture was brought to reflux and maintained for 48 hours. The reaction product was filtered, washed with acetonitrile and evaporated for removal of solvent. The product was passed through a silica gel chromatographic column using dichloromethane eluent, for recovery of 0.25 gram (20% yield) of a biphenol ether compound having the following formula confirmed by TLC, IR and mass spectral analyses: ##STR26## to reflux maintained for 48 hours The reaction product was filtered washed with acetonitrile evaporated for removal of solvent

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

Procedure: Nine grams (0.05 mole) of 1-bromo-2-butoxy-ethane and 6.1 grams (0.05 mole) of 4-hydroxybenzaldehyde were dissolved in 75 mls. of acetonitrile. Into the mixture were added 13.8 grams (0.1 mole) of finely ground potassium carbonate and the resulting reaction mixture was stirred under reflux for ten hours. The reaction mixture was allowed to cool, was filtered, washed with acetonitrile and evaporated to an amber oily product. The product was passed through a silica gel chromatographic column for recovery of a colorless oil (64% yield) having the following structure: ##STR20## the resulting reaction mixture under reflux for ten hours to cool was filtered washed with acetonitrile evaporated to an amber oily product

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

Procedure: To a 1 l three-neck flask were added 70 g of sodium salt of p-hydroxybenzoic acid ##STR4## and 200 ml of N,N-dimethylformamide, and the contents were heated under reflux. To the heated contents, 50 g of β-n-butoxyethyl bromide was dropped over a period of 30 minutes and heating was continued under reflux for further 8 hours. After cooling with water, 300 ml of water and 200 ml of toluene were added to the contents and after shaking, the resulting organic layer was separated, washed with 4 N hydrochloric acid and then with a 20% aqueous solution of sodium hydroxide. After distilling off toluene and heating the remaing material together with 200 ml of a 20% aqueous solution of sodium hydroxide for 3 hours, the resulting material was neutralized with hydrochloric acid to precipitate the objective material. After washing with water, the objective material was recrystallized from ethanol to obtain 55 g of p-(β-n-butoxy)ethoxybenzoic acid. The melting point of this material was 114.5°-115° C. and the values of the elemental analysis thereof showed a good agreement with the calculated values as seen below. under reflux heating under reflux for further 8 hours were added to the contents the resulting organic layer was separated washed with 4 N hydrochloric acid After distilling off toluene heating the remaing material together with 200 ml of a 20% aqueous solution of sodium hydroxide for 3 hours to precipitate the objective material After washing with water the objective material was recrystallized from ethanol