4-propan-2-ylsulfanylphenol

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

Procedure: A solution of 4-(1-methylethylthio)phenol (16.83 g., 0.1 mole) in 150 ml. of isopropyl alcohol is treated with 5.2 ml. of 50% sodium hydroxide solution (0.10 mole) and 2 ml. of water. To this mixture is added in one portion 1-bromo-3-chloropropane (16.5 g., 0.105 mole) and the mixture stirred and refluxed for a period of 20 hrs. After cooling, the reaction mixture is concentrated under reduced pressure and the resulting residue extracted with ether. The ethereal extract is filtered, concentrated under reduced pressure and the oily residue distilled affording 4.8 g. (20% yield) of 1-chloro-3-[4-(1-methylethylthio)phenoxy]propane, b.p. 136°-140° C. at 0.6 mm Hg. refluxed for a period of 20 hrs After cooling the reaction mixture is concentrated under reduced pressure the resulting residue extracted with ether The ethereal extract is filtered concentrated under reduced pressure the oily residue distilled affording 4.8 g

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

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: A solution of 4-(1-methylethylthio)phenol (16.83 g., 0.1 mole) in 150 ml. of isopropyl alcohol is treated with 5.2 ml. of 50% sodium hydroxide solution (0.10 mole) and 2 ml. of water. To this mixture is added in one portion 1-bromo-3-chloropropane (16.5 g., 0.105 mole) and the mixture stirred and refluxed for a period of 20 hrs. After cooling, the reaction mixture is concentrated under reduced pressure and the resulting residue extracted with ether. The ethereal extract is filtered, concentrated under reduced pressure and the oily residue distilled affording 4.8 g. (20% yield) of 1-chloro-3-[4-(1-methylethylthio)phenoxy]propane, b.p. 136°-140° C. at 0.6 mm Hg. refluxed for a period of 20 hrs After cooling the reaction mixture is concentrated under reduced pressure the resulting residue extracted with ether The ethereal extract is filtered concentrated under reduced pressure the oily residue distilled affording 4.8 g

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

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

Procedure: A solution of 4-(1-methylethylthio)phenol (16.83 g., 0.1 mole) in 150 ml. of isopropyl alcohol is treated with 5.2 ml. of 50% sodium hydroxide solution (0.10 mole) and 2 ml. of water. To this mixture is added in one portion 1-bromo-3-chloropropane (16.5 g., 0.105 mole) and the mixture stirred and refluxed for a period of 20 hrs. After cooling, the reaction mixture is concentrated under reduced pressure and the resulting residue extracted with ether. The ethereal extract is filtered, concentrated under reduced pressure and the oily residue distilled affording 4.8 g. (20% yield) of 1-chloro-3-[4-(1-methylethylthio)phenoxy]propane, b.p. 136°-140° C. at 0.6 mm Hg. refluxed for a period of 20 hrs After cooling the reaction mixture is concentrated under reduced pressure the resulting residue extracted with ether The ethereal extract is filtered concentrated under reduced pressure the oily residue distilled affording 4.8 g

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

Procedure: Reaction of the epichlorohydrin derivative of 4-(isopropylthio)phenol (9.0 g., 0.04 mole) with cyclohexylbutylamine (6.7 g., 0.043 mole) according to procedure of Example 2(b) and crystallization of the crude product from ethanol affords an 11.4% yield of analytically pure 1-[(4-cyclohexylbutyl)amino]-3-[4-[(1-methylethyl)thio]phenoxy]-2-propanol hydrochloride, m.p. 179° with prior softening from 118°. according to procedure of Example 2(b) and crystallization of the crude product from ethanol

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

Procedure: Reaction of the epichlorohydrin derivative of 4-(isopropylthio)phenol (5.0 g., 0.022 mole) with cyclohexylethylamine (3.3 g., 0.026 mole) according to the procedure of Example 2(b) and crystallization of the crude product from isopropyl alcohol affords an 18% yield of analytically pure 1-[(2-cyclohexylethyl)amino]-3-[4-[(1-methylethyl)thio]phenoxy]-2-propanol hydrochloride, m.p. 180°-182° (corr.). according to the procedure of Example 2(b) and crystallization of the crude product from isopropyl alcohol