(3-methylsulfanylphenyl)methanol

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

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

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

Procedure: The title compound was prepared according to the process described in Example 183 via the intermediates (3-methylsulfanylphenyl)methanol (MS (ESI+): 155) and (3-methylsulfanylphenyl)acetonitrile (MS (ESI+): 164). In step c), the reaction mixture was not heated under reflux after the addition of the methyl acrylate, but stirred for 16 h at room temperature. From 2.9 g of (3-methylsulfanylphenyl)acetonitrile, 0.85 g of the title compound was obtained. The title compound was prepared In step c), the reaction mixture was not heated under reflux

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

Procedure: To a solution of (3-methylsulfanyl-phenyl)-methanol (23.8 g, 0.156 mol) in benzene (250 mL) was added thionyl chloride (26.9 g, 0.234 mol) under cooling with an ice-bath. The ice-bath was removed and the reaction mixture stirred for 48 hours at room temperature. The solution was concentrated and used without further work-up (26.9 g). under cooling with an ice-bath The ice-bath was removed The solution was concentrated

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

Procedure: To a suspension of 3-methylsulfanyl-benzoic acid (38 g, 0.226 mol) in Toluene (500 mL) was added 200 mL of Red-Al® dropwise at 50° C. over 30 minutes. After stirring at room temperature for 3 hours, NaOH 10% (250 mL) was added while cooling with an ice-bath and then stirred overnight. The organic layer was separated and the water layer extracted twice with toluene (2×100 mL). The combined organic layers were dried (K2CO3), concentrated and distilled under reduced pressure to give the desired product (23.8 g, 68%). MS: 152,7 (M+131 ). while cooling with an ice-bath stirred overnight The organic layer was separated the water layer extracted twice with toluene (2×100 mL) The combined organic layers were dried (K2CO3) concentrated distilled under reduced pressure

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

Procedure: To a solution of (3-methylsulfanyl-phenyl)-methanol (23.8 g, 0.156 mol) in benzene (250 mL) was added thionyl chloride (26.9 g, 0.234 mol) under cooling with an ice-bath. The ice-bath was removed and the reaction mixture stirred for 48 hours at room temperature. The solution was concentrated and used without further work-up (26.9 g). under cooling with an ice-bath The ice-bath was removed The solution was concentrated

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

Procedure: To a suspension of 3-methylsulfanyl-benzoic acid (38 g, 0.226 mol) in Toluene (500 mL) was added 200 mL of Red-Al® dropwise at 50° C. over 30 minutes. After stirring at room temperature for 3 hours, NaOH 10% (250 mL) was added while cooling with an ice-bath and then stirred overnight. The organic layer was separated and the water layer extracted twice with toluene (2×100 mL). The combined organic layers were dried (K2CO3), concentrated and distilled under reduced pressure to give the desired product (23.8 g, 68%). MS: 152,7 (M+131 ). while cooling with an ice-bath stirred overnight The organic layer was separated the water layer extracted twice with toluene (2×100 mL) The combined organic layers were dried (K2CO3) concentrated distilled under reduced pressure

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

Procedure: 3-Hydroxymethyl-1-methylthiobenzene (3.3 g, 21 mmol) is dissolved in absolute CH2Cl2 (20 ml) under an argon atmosphere. A solution of SOC12 (2.6 g, 21 mmol) in absolute CH2Cl2 (10 ml) is added dropwise with stirring to this initial mixture in the course of 15 min, initially 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%) initially 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: 3-Hydroxymethyl-1-methylthiobenzene (3.3 g, 21 mmol) is dissolved in absolute CH2Cl2 (20 ml) under an argon atmosphere. A solution of SOC12 (2.6 g, 21 mmol) in absolute CH2Cl2 (10 ml) is added dropwise with stirring to this initial mixture in the course of 15 min, initially 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%) initially 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: The title compound was prepared according to the process described in Example 183 via the intermediates (3-methylsulfanylphenyl)methanol (MS (ESI+): 155) and (3-methylsulfanylphenyl)acetonitrile (MS (ESI+): 164). In step c), the reaction mixture was not heated under reflux after the addition of the methyl acrylate, but stirred for 16 h at room temperature. From 2.9 g of (3-methylsulfanylphenyl)acetonitrile, 0.85 g of the title compound was obtained. The title compound was prepared In step c), the reaction mixture was not heated under reflux