1-(4-chlorophenyl)ethanol

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: There were weighed out p-chlorophenyl-ethanol (5, racemic compound) (78 mg, 0.05 mmol) and (S)-(−)-3,3,5,5-tetramethyl-4H-dinaphtho[2,1-c:1′,2′-e]-azepin-N-oxyl (1.8 mg, 0.05 mmol). Then, 2 ml of acetone was added to obtain a uniform solution. Added thereto was 250 mg of silica gel (product of Merck, grade 9385) and the mixture was vigorously agitated for 5 minutes. The acetone used was distilled off under reduced pressure. Added thereto was 7% aqueous solution of sodium bicarbonate (5 ml) containing 20 wt. % of sodium bromide. Then, the mixture was thoroughly stirred. Two platinum electrodes (1.5×1.0 cm) were applied to the mixture which was then subjected to electrolytic oxidation reaction for 0.68 hour while being vigorously stirred at −15° C. and maintaining the current at 30 mA (quantity of electricity being 2.2 F/mol). After completion of reaction, silica gel was filtered off from the reaction mixture, extraction was effected with 5 ml of acetone and acetone was distilled off. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=7/1), giving p-chloroacetophenone (6) [39 mg, yield 100% based on the starting compound (5a)] and the starting compound (5b) (38 m, recovery percentage 97%, optical purity 83%). to obtain a uniform solution Added The acetone used was distilled off under reduced pressure Added containing 20 wt. % of sodium bromide Then, the mixture was thoroughly stirred was then subjected to electrolytic oxidation reaction for 0.68 hour while being vigorously stirred at −15° C. maintaining the current at 30 mA (quantity of electricity being 2.2 F/mol) After completion of reaction, silica gel was filtered off from the reaction mixture, extraction was distilled off The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=7/1)

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

Procedure: As shown here, the biochemical conversion reaction of immobilized buckwheat protein for the substrate (±)-1-(4-chlorophenyl)ethanol (200 mg) requires 13 days by going through bioconversion to 4-chloroacetophenone accompanying sterically selective oxidation of (S)-1-(4-chlorophenyl)ethanol to obtain 116 mg of (R)-1-(4-chlorophenyl)ethanol at a yield of 58%. Optical purity was obtained at 91% e.e.

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

Procedure: As shown here, the biochemical conversion reaction of immobilized soy bean protein for the substrate (±)-1-(4-chlorophenyl)ethanol (200 mg) requires 3 days by going through bioconversion to 4-chloroacetophenone accompanying sterically selective oxidation of (S)-1-(4-chlorophenyl)ethanol to obtain 102 mg of (R)-1-(4-chlorophenyl)ethanol at a yield of 51%. Optical purity was obtained at 96% e.e.

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

Procedure: As shown here, the biochemical conversion reaction of immobilized green pea protein for the substrate (±)-1-(4-chlorophenyl)ethanol (200 mg) requires 8 days by going through bioconversion to 4-chloroacetophenone accompanying sterically selective oxidation of (R)-1-(4-chlorophenyl)ethanol to obtain 84 mg of (S)-1-(4-chlorophenyl)ethanol at a yield of 42%. Optical purity was obtained at 87% e.e.

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

Procedure: By using the equipment analysis described above, the retention times of (±)-1-(4-bromophenyl)ethanol were confirmed to be 10.447 for the S form and 11.031 for the R form, those of (±)-1-(4-chlorophenyl)ethanol 9.936 for the S form and 10.355 for the R form, those of (±)-1-phenylethanol 11.958 for the S form and 13.133 for the R form, those of (±)-1-(2-naphthyl)ethanol 15.693 for the S form and 17.049 for the R form, those of (±)-1-(4-methoxyphenyl)ethanol 9.165 for the S form and 10.781 for the R form, and those of (±)-1-(4-nitrophenyl)ethanol 18.923 for the R form and 19.562 for the S form. In addition, the retention times of 4-bromoacetophenone, 4-chloroacetophenone, 4-methoxyacetophenone and 4-nitroacetophenone that are formed by oxidation of each substrate were similarly confirmed to be 13.122, 10.304, 17.169 and 37.208, respectively.

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: There were weighed out p-chlorophenyl-ethanol (5, racemic compound) (78 mg, 0.05 mmol) and (S)-(−)-3,3,5,5-tetramethyl-4H-dinaphtho[2,1-c:1′, 2′-e]-azepin-N-oxyl (1.8 mg, 0.05 mmol). Then, 2 ml of acetone was added to obtain a uniform solution. Added thereto was 250 mg of silica gel (product of Merck, grade 9385) and the mixture was vigorously agitated for 5 minutes. The acetone used was distilled off under reduced pressure. Added thereto was 7% aqueous solution of sodium bicarbonate (5 ml) containing 20 wt. % of sodium bromide. Then, the mixture was thoroughly stirred. Two platinum electrodes (1.5×1.0 cm2) were applied to the mixture which was then subjected to electrolytic oxidation reaction for 0.68 hour while being vigorously stirred at −15° C. and maintaining the current at 30 mA (quantity of electricity being 2.2 F/mol). After completion of reaction, silica gel was filtered off from the reaction mixture, extraction was effected with 5 ml of acetone and acetone was distilled off. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=7/1), giving p-chloroacetophenone (6) [39 mg, yield 100% based on the starting compound (5a)] and the starting compound (5b) (38 m, recovery percentage 97%, optical purity 83%). to obtain a uniform solution Added The acetone used was distilled off under reduced pressure Added containing 20 wt. % of sodium bromide Then, the mixture was thoroughly stirred was then subjected to electrolytic oxidation reaction for 0.68 hour while being vigorously stirred at −15° C. maintaining the current at 30 mA (quantity of electricity being 2.2 F/mol) After completion of reaction, silica gel was filtered off from the reaction mixture, extraction was distilled off The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=7/1)

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

Procedure: There were weighed out p-chlorophenyl-ethanol (5, racemic compound) (78 mg, 0.05 mmol) and (S)-(−)-3,3,5,5-tetramethyl-4H-dinaphtho[2,1-c:1′, 2′-e]-azepin-N-oxyl (1.8 mg, 0.05 mmol). Then, 2 ml of acetone was added to obtain a uniform solution. Added thereto was 250 mg of silica gel (product of Merck, grade 9385) and the mixture was vigorously agitated for 5 minutes. The acetone used was distilled off under reduced pressure. Added thereto was 7% aqueous solution of sodium bicarbonate (5 ml) containing 20 wt. % of sodium bromide. Then, the mixture was thoroughly stirred. Two platinum electrodes (1.5×1.0 cm2) were applied to the mixture which was then subjected to electrolytic oxidation reaction for 0.68 hour while being vigorously stirred at −15° C. and maintaining the current at 30 mA (quantity of electricity being 2.2 F/mol). After completion of reaction, silica gel was filtered off from the reaction mixture, extraction was effected with 5 ml of acetone and acetone was distilled off. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=7/1), giving p-chloroacetophenone (6) [39 mg, yield 100% based on the starting compound (5a)] and the starting compound (5b) (38 m, recovery percentage 97%, optical purity 83%). to obtain a uniform solution Added The acetone used was distilled off under reduced pressure Added containing 20 wt. % of sodium bromide Then, the mixture was thoroughly stirred was then subjected to electrolytic oxidation reaction for 0.68 hour while being vigorously stirred at −15° C. maintaining the current at 30 mA (quantity of electricity being 2.2 F/mol) After completion of reaction, silica gel was filtered off from the reaction mixture, extraction was distilled off The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=7/1)

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

Procedure: Prepared according to the procedure described in Example 56, Step 1, using the following starting materials: 1-(4-chlorophenyl)ethanol and phosgene (20% in toluene). Prepared