1-phenylethane-1,2-diol

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:

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 100 g (0.63 mol) of (±)-1-phenyl-1,2-ethanediol (3) (87% pure according to GC) according to Example 1, 200 ml of toluene, 32 g (0.24 mol) of paraldehyde and 1 g of para-toluenesulfonic acid were charged to a 1 l stirrer, heated to boiling (110° C.) and stirred under reflux for a period of 4 h. A total of 10 ml of water were eliminated. After this time, the mixture was cooled to 20° C. and washed until neutral with sodium carbonate solution and water, and the solvent was distilled off under reduced pressure, leaving 103 g of crude product (85.3% pure according to GC). GC conditions see Example 2. were charged to a 1 l stirrer heated (110° C.) under reflux for a period of 4 h washed until neutral with sodium carbonate solution and water the solvent was distilled off under reduced pressure

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 1 l stirrer fitted with reflux condenser, thermometer and dropping funnel was charged with 223 g (1.47 mol) of (±)-1-phenyl-1,2-ethanediol (3) (91% pure according to GC) from Example 1, 100 ml of diethyl ether and 2 g of para-toluenesulfonic acid and cooled to 5–10° C., and, at this temperature, 80.8 g (1.83 mol) of acetaldehyde were added over the course of 30 min. When the dropwise addition was complete, the mixture was then stirred firstly for 4 h at 5–10° C. and for a further 2 h at a maximum of 20° C. After this time, water was added, the organic phase was separated off, the aqueous phase was extracted with 1×100 ml of ether, and the combined organic phases were washed until neutral with sodium carbonate solution and water. Drying over Na2SO4 was then carried out, and the solvent was distilled off under reduced pressure. A 1 l stirrer fitted with reflux condenser cooled to 5–10° C. When the dropwise addition the organic phase was separated off the aqueous phase was extracted with 1×100 ml of ether the combined organic phases were washed until neutral with sodium carbonate solution and water Drying over Na2SO4 the solvent was distilled off under reduced pressure

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

Procedure: A 2 l stirrer fitted with reflux condenser, thermometer and dropping funnel was charged with 600 g of 0.1% strength H2SO4 and 2 g of tetrabutylammonium hydrogensulfate, and then, at 20° C. to 25° C., 200 g (1.67 mol) of styrene oxide (2) were added over the course of 1 h. When the dropwise addition was complete, the mixture was then stirred for 2 h and then worked up. 200 ml of diethyl ether were added to the reaction mixture, and the organic phase was washed until neutral with sodium carbonate solution and water, and dried over Na2SO4, and the solvent was distilled off under reduced pressure, leaving 223 g of crude product (91% pure according to GC). A 2 l stirrer fitted with reflux condenser When the dropwise addition the organic phase was washed until neutral with sodium carbonate solution and water dried over Na2SO4 the solvent was distilled off under reduced pressure

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

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

Procedure: A mixture of 1-phenyl-1,2-ethanediol (1.38 g, 10 mmole), immidazole (817 mg, 12 mmole), and tert-butylchlorodimethylsilane (1.81 g, 12 mmole) in DMF 15 (ml) was stirred at 0° C. for 1.5 hrs and then at room temperature overnight. The resulting mixture was diluted with ethyl acetate, washed with water, brine, and dried over sodium sulfate. After removal of the solvent, the residue was purified by silica gel column chromatography using ethyl acetate-hexane (1:4) as eluent. 2-(tert-butyidimethylsilyl)oxy-1-phenylethanol was obtained as an oil (2.6 g, 100% yield). at room temperature overnight washed with water, brine dried over sodium sulfate After removal of the solvent the residue was purified by silica gel column chromatography

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

Procedure: A mixture of 1-phenyl-1,2-ethanediol (1.38 g, 10 mmole), immidazole (817 mg, 12 mmole), and tert-butylchlorodimethylsilane (1.81 g, 12 mmole) in DMF 15 (ml) was stirred at 0° C. for 1.5 hrs and then at room temperature overnight. The resulting mixture was diluted with ethyl acetate, washed with water, brine, and dried over sodium sulfate. After removal of the solvent, the residue was purified by silica gel column chromatography using ethyl acetate-hexane (1:4) as eluent. 2-(tert-butyidimethylsilyl)oxy-1-phenylethanol was obtained as an oil (2.6 g, 100% yield). at room temperature overnight washed with water, brine dried over sodium sulfate After removal of the solvent the residue was purified by silica gel column chromatography

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Pd/C (5 mol %) is weighed into a reaction flask. A solvent mixture consisting of ethanol and water (4:1) and ammonium formate (30 mol %) is added, the reaction flask is capped with a rubber septa and the mixture is heated (80° C.) for 2 minutes. Formic acid (3 equivalents) and then benzyl alcohol are added by syringe. The reaction is run for 10-40 minutes and the reaction is quenched with brine. The product is extracted by DCM and the organic phase is dried by Na2SO4. The product 1-phenyl-2-propanol was analyzed by 1H NMR and produced in 60% yield. is added the reaction flask is capped with a rubber septa the reaction is quenched with brine The product is extracted by DCM the organic phase is dried by Na2SO4 produced in 60% yield

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

Procedure: Into a 250-mL 3-necked round-bottom flask was placed a solution of 1-phenylethane-1,2-diol (10 g, 72.38 mmol, 1.00 equiv), TBSCl (22 g, 145.97 mmol, 2.00 equiv) and triethylamine (14.7 g, 145.27 mmol, 2.00 equiv) in tetrahydrofuran (100 mL). The solution was stirred overnight at room temperature. The next day it was diluted with 150 mL of H2O and the mixture was extracted with 3×80 mL of ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1/10). Purification afforded 17 g (93%) of 2-[(tert-butyldimethylsilyl)oxy]-1-phenylethan-1-ol as a white oil. Into a 250-mL 3-necked round-bottom flask was placed the mixture was extracted with 3×80 mL of ethyl acetate dried over anhydrous sodium sulfate concentrated under vacuum Purification