2-(4-methylsulfanylphenyl)ethanol

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

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

Procedure: 3-(4-Hydroxyphenyl)-2-phenoxypropanoic acid methyl ester was reacted with 2-(4-methylsulfanylphenyl)ethanol using the same methods as in Example 38(c) to give 3-{4-[2-(4-methylsulfanylphenyl)ethoxy]phenyl}-2-phenoxy-propanoic acid methyl ester.

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

Procedure: 4-(methylthio)benzeneethanol (7.44 g) and 1,5 dibromopentane (30.48 g) were stirred rapidly at room temperature with TAB (1.0 g) and 12.5M aqueous sodium hydroxide (35 ml) for 64 h. The mixture was diluted with water (170 ml), extracted with ER (3×200 ml), and the combined organic extracts were washed consecutively with water (170 ml) and brine (170 ml), dried and evaporated. The residual oil (29.29 g) was purified by FCC eluting with ER-CX (0:100→3:97) to give the title compound as a colourless oil (10.68 g). T.l.c. (ER-CX 1:79) Rf 0.08. extracted with ER (3×200 ml) the combined organic extracts were washed consecutively with water (170 ml) and brine (170 ml) dried evaporated The residual oil (29.29 g) was purified by FCC eluting with ER-CX (0:100→3:97)

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

Procedure: 4-(methylthio)benzeneethanol (7.44 g) and 1,5 dibromopentane (30.48 g) were stirred rapidly at room temperature with TAB (1.0 g) and 12.5M aqueous sodium hydroxide (35 ml) for 64 h. The mixture was diluted with water (170 ml), extracted with ER (3×200 ml), and the combined organic extracts were washed consecutively with water (170 ml) and brine (170 ml), dried and evaporated. The residual oil (29.29 g) was purified by FCC eluting with ER-CX (0:100→3:97) to give the title compound as a colourless oil (10.68 g). T.l.c. (ER-CX 1:79) Rf 0.08. extracted with ER (3×200 ml) the combined organic extracts were washed consecutively with water (170 ml) and brine (170 ml) dried evaporated The residual oil (29.29 g) was purified by FCC eluting with ER-CX (0:100→3:97)

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

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

Procedure: 6.27 g of 4-methylthiophenethyl alcohol in 100 ml of dimethyl sulfoxide were treated with 3.58 g of a 50% sodium hydride dispersion in mineral oil and the mixture was stirred at 60° C. for 10 minutes. 3.53 g of chloroacetic acid were added and the heating was continued at 80° C. for 3 hours while stirring. The mixture was cooled, poured into water and washed with ethyl acetate. The aqueous phase was acidified to pH 1 with concentrated hydrochloric acid and extracted with ethyl acetate. The organic phase was separated, washed well with water, dried over sodium sulfate, filtered and evaporated to dryness. The residue was recrystallized from toluene/hexane to give 3.89 g (46%) of 2-(4-methylthiophenyl)ethoxyacetic acid of melting 58°-60° C. the heating was continued at 80° C. for 3 hours while stirring The mixture was cooled washed with ethyl acetate extracted with ethyl acetate The organic phase was separated washed well with water dried over sodium sulfate filtered evaporated to dryness The residue was recrystallized from toluene/hexane

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

Procedure: 4-(Methylthio)benzeneethanol (7.44 g) and 1,5 dibromopentane (30.48 g) were stirred rapidly at room temperature with TAB (1.0 g) and 12.5M aqueous sodium hydroxide (35 ml) for 64 h. The mixture was diluted with water (170 ml), extracted with ER (3×200 ml) and the combined organic extracts were washed consecutively with water (170 ml) and brine (170 ml), dried and evaporated. The residual oil (29.29 g) was purified by FCC eluting with ER-CX (0:100→3:97) to give the title compound as a colourless oil (10.68 g). T.l.c. (ER-CX 1:79) Rf 0.08. extracted with ER (3×200 ml) the combined organic extracts were washed consecutively with water (170 ml) and brine (170 ml) dried evaporated The residual oil (29.29 g) was purified by FCC eluting with ER-CX (0:100→3:97)

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

Procedure: 1.7 g (10 mmole) 2-[4-(methylsulfanyl)phenyl]-1-ethanol, 5.24 g (20 mmole) triphenylphosphine and 5.05 g (20 mmole) 1,1-(azodicarbonyl)dipiperidine was added to a mixture of 2.47 g (20 mmole) 4-hydroxybenzaldehyde in 40 ml dichloromethane under argon atmosphere. Stirring at room temperature for 2 hours, (more dichloromethane was added after 20 minutes), gave a solid material that was removed by filtration. The filtrate was purified by chromatography on silica gel using dichloromethane as eluent to give 2.3 g (yield 84.4%) of 4-[2-(4-methylmercaptophenyl)ethoxy]benzaldehyde. gave a solid material that was removed by filtration The filtrate was purified by chromatography on silica gel

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

Procedure: 5.5 ml 1 M borane-tetrahydrofuiran complex was slowly added to a solution of 1 g (5.5 mmole) 4-(methylmercapto)phenyl acetic acid in 5 ml tetrahydrofuran at −10° C. The reaction mixture was allowed to reach room temperature and the reaction was followed by TLC. After completion 10 ml methanol was added and the solvents were evaporated. Diethyl ether and 2 M sodium hydroxide was added, the phases were separated, the organic phase was dried, filtered and evaporated in vacuo to give 0.8 g (yield 84.4%) of 2-[4-(methylmercapto)phenyl]-1-ethanol. to reach room temperature the solvents were evaporated Diethyl ether and 2 M sodium hydroxide was added the phases were separated the organic phase was dried filtered evaporated in vacuo

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

Procedure: 3-(4-Hydroxyphenyl)-2-phenoxypropanoic acid methyl ester was reacted with 2-(4-methylsulfanylphenyl)ethanol using the same methods as in Example 38(c) to give 3-{4-[2-(4-methylsulfanylphenyl)ethoxy]phenyl}-2-phenoxy-propanoic acid methyl ester.

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

Procedure: 4-(methylthio)benzeneethanol (7.44 g) and 1,5 dibromopentane (30.48 g) were stirred rapidly at room temperature with TAB (1.0 g) and 12.5M aqueous sodium hydroxide (35 ml) for 64 h. The mixture was diluted with water (170 ml), extracted with ER (3×200 ml), and the combined organic extracts were washed consecutively with water (170 ml) and brine (170 ml), dried and evaporated. The residual oil (29.29 g) was purified by FCC eluting with ER-CX (0:100→3:97) to give the title compound as a colourless oil (10.68 g). T.l.c. (ER-CX 1:79) Rf 0.08. extracted with ER (3×200 ml) the combined organic extracts were washed consecutively with water (170 ml) and brine (170 ml) dried evaporated The residual oil (29.29 g) was purified by FCC eluting with ER-CX (0:100→3:97)