(2-methylsulfanylphenyl)methanol

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

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

Procedure: 5 g of 2-methylsulfanylbenzoic acid were dissolved in 50 ml of toluene, treated in portions at 20° C. with 14.5 ml of a solution of sodium dihydridobis(2-methoxy-ethoxy)aluminate (Red-AI®; 65% strength in toluene) and stirred for 5 h. The reaction mixture was added to 200 ml of water and extracted three times with 100 ml each of EA. The combined organic phases were dried with magnesium sulfate and the solvent was removed in vacuo. 4.6 g of the crude title compound were obtained as a brown oil. extracted three times with 100 ml each of EA The combined organic phases were dried with magnesium sulfate the solvent was removed in vacuo

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Phosphorus tribromide (75 g) in toluene (50 ml) was added to a stirred mixture of 2-methylthiobenzyl alcohol (42.5 g) in toluene (25 ml) over 10 minutes at 5° C. The mixture was then stirred at 40° C. for 1 hour, water (100 ml) was added and stirring continued at ambient temperature for 1 hour. The organic layer was separated and the aqueous layer extracted with ethyl acetate. The combined organic layers yielded an oil. The oil (58.6 g) was dissolved in a 1:2 mixture of water and ethanol and sodium cyanide (26.5 g) was added over 15 minutes. The mixture was stirred at 50° C. for 1.5 hours then poured onto water (500 ml) and extracted with ethyl acetate. The extract yielded 2-methylthiophenylacetonitrile. stirring continued at ambient temperature for 1 hour The organic layer was separated the aqueous layer extracted with ethyl acetate The combined organic layers yielded an oil was added over 15 minutes The mixture was stirred at 50° C. for 1.5 hours then poured onto water (500 ml) extracted with ethyl acetate

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

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

Procedure: 5 g of 2-methylsulfanylbenzoic acid were dissolved in 50 ml of toluene, treated in portions at 20° C. with 14.5 ml of a solution of sodium dihydridobis(2-methoxy-ethoxy)aluminate (Red-AI®; 65% strength in toluene) and stirred for 5 h. The reaction mixture was added to 200 ml of water and extracted three times with 100 ml each of EA. The combined organic phases were dried with magnesium sulfate and the solvent was removed in vacuo. 4.6 g of the crude title compound were obtained as a brown oil. extracted three times with 100 ml each of EA The combined organic phases were dried with magnesium sulfate the solvent was removed in vacuo

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

Procedure: 2-Hydroxymethyl-1-methylthiobenzene (3.3 g, 21 mmol) is dissolved in 20 ml of absolute CH2Cl2 under an argon atmosphere. A solution of SOCl2 (2.6 g, 21 mmol) in 10 ml of absolute CH2Cl2 is added dropwise with stirring to this initial mixture in the course of 15 min, first under reflux, then at an internal temperature of 30° C. The reaction mixture is stirred under reflux for 2.25 h. The reaction mixture is concentrated and the oily crude product is purified by bulb tube distillation (7.9×10−2 mbar, 125-140° C.): colorless oil; yield: 3.3 g (88%). first under reflux at an internal temperature of 30° C under reflux for 2.25 h The reaction mixture is concentrated the oily crude product is purified by bulb tube distillation (7.9×10−2 mbar, 125-140° C.)

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

Procedure: To a solution of (2-methylsulfanylphenyl)methanol (0.20 g, 1.3 mmol) obtained in Step 1 in dichloromethane (4.0 mL), Celite (0.40 g) and pyridinium chlorochromate (0.42 g, 1.9 mmol) were added, followed by stirring at room temperature for 1.0 hour. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5 to 80/20) to obtain 2-methylsulfanylbenzaldehyde (0.14 g, 69%). The reaction mixture was filtered the filtrate was concentrated under reduced pressure The residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5 to 80/20)

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

Procedure: To a solution of 2-methylsulfanylbenzoic acid methyl ester (0.30 g, 1.7 mmol) in toluene (3.0 mL), diisobutylaluminum hydride (0.94 mol/L toluene solution, 3.9 mL, 3.7 mmol) was added dropwise at −78° C. and the solution was stirred for 3.5 hours. The reaction mixture was added with 2-propanol (0.20 mL), warmed to 0° C., and added with saturated aqueous potassium sodium tartrate solution to separate the mixture into organic layer and aqueous layer. The obtained organic layer was concentrated under reduced pressure and the residue was purified by silica gel chromatography (hexane/ethyl acetate=90/10 to 70/30) to obtain (2-methylsulfanylphenyl)methanol (0.22 g, 87%). to separate the mixture into organic layer and aqueous layer The obtained organic layer was concentrated under reduced pressure the residue was purified by silica gel chromatography (hexane/ethyl acetate=90/10 to 70/30)

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

Procedure: To a solution of 1.00 g (6.57 mmol) of 2-methylsulfanylbenzaldehyde in 10 mL of ethanol at 0° C. was added 250 mg of NaBH4. The reaction was stirred at 0° C. for 10 min, then diluted with 50 mL of water. The aqueous suspension was extracted with diethyl ether (3×15 mL), then the combined ether layers were back extracted with brine (1×10 mL), dried over MgSO4, filtered, and concentrated in vacuo to 1.01 g (100%) of the titled compound as an oil. The aqueous suspension was extracted with diethyl ether (3×15 mL) the combined ether layers were back extracted with brine (1×10 mL) dried over MgSO4 filtered concentrated in vacuo to 1.01 g (100%) of the titled compound as an oil

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

Procedure: To a solution of 400 mg (2.59 mmol) of 2-methylthio-benzylalcohol in 8 mL of methanol was added 1.42 g (3.37 mmol) of triphenylphosphine dibromide and stirred at room temperature for 18 h. The mixture was concentrated and purified by silica gel flash chromatography, eluting with 2% ethyl acetate/hexane to give 289 mg of the title compound. NMR (CDCl3): δ 2.50 (s, 3H), 4.63 (s, 2H), 7.13 (m, 1H), 7.27 (m, 2H), 7.34 (d, 1). The mixture was concentrated purified by silica gel flash chromatography eluting with 2% ethyl acetate/hexane

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Phosphorus tribromide (75 g) in toluene (50 ml) was added to a stirred mixture of 2-methylthiobenzyl alcohol (42.5 g) in toluene (25 ml) over 10 minutes at 5° C. The mixture was then stirred at 40° C. for 1 hour, water (100 ml) was added and stirring continued at ambient temperature for 1 hour. The organic layer was separated and the aqueous layer extracted with ethyl acetate. The combined organic layers yielded an oil. The oil (58.6 g) was dissolved in a 1:2 mixture of water and ethanol and sodium cyanide (26.5 g) was added over 15 minutes. The mixture was stirred at 50° C. for 1.5 hours then poured onto water (500 ml) and extracted with ethyl acetate. The extract yielded 2-methylthiophenylacetonitrile. stirring continued at ambient temperature for 1 hour The organic layer was separated the aqueous layer extracted with ethyl acetate The combined organic layers yielded an oil was added over 15 minutes The mixture was stirred at 50° C. for 1.5 hours then poured onto water (500 ml) extracted with ethyl acetate