No renderable structure data available
CC(=O)C(CC1=CC=C(C=C1)Cl)C2=CC=CC=C2Chemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 4-(4-chlorophenyl)-3-phenylbutan-2-one |
|---|---|
| IUPAC Name | — |
| CAS Number | 4863-70-1 |
| Database ID | 229369 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
4-(4-chlorophenyl)-3-phenylbutan-2-one (CAS 4863-70-1) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 229369
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-281993cdaa9a48bf80c747150d6bc2c0Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 4-(4-chlorophenyl)-3-phenyl-2-butanone (Step D, 13 g, 50 mmol) in MeOH (100 mL) at 0° C. was added sodium borohydride (3.8 g, 100 mmol). After stirring at 0° C. for 30 min, the reaction was quenched by addition of 2 M hydrochloric acid (50 mL). The volatile materials were removed by concentrating on a rotary evaporator and the residue partitioned between water (100 mL) and EtOAc (200 mL). The organic layer was separated and the aqueous layer extracted with EtOAc (2×200 mL). The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to dryness to give the crude product, which was purified by flash column chromatography on silica gel eluted with 10% EtOAc in hexane to afford the pure faster eluting isomer and a mixture containing both the faster eluting isomer and the slower eluting isomer. Faster eluting isomer: 1H NMR (500 MHz, CD3OD): δ 7.25-7.00 (m, 9H), 4.00 (m, 1H), 3.15 (m, 1H), 2.97 (m, 1H), 2.85 (m, 1H), 1.10 (d, 3H). the reaction was quenched by addition of 2 M hydrochloric acid (50 mL) The volatile materials were removed by concentrating on a rotary evaporator the residue partitioned between water (100 mL) and EtOAc (200 mL) The organic layer was separated the aqueous layer extracted with EtOAc (2×200 mL) The combined organic extracts were washed with brine dried over anhydrous sodium sulfate filtered concentrated to dryness
Source ID: ord-2f70beb27aff45bd805b5d885df38187Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of N-methoxy-N-methyl-3-(4-chlorophenyl)-2-phenylpropanamide (Step C, 16 g, 53 mmol, dried by azeotroping with toluene) in anhydrous THF (200 mL) at 0° C. was added methylmagnesium bromide (3 M in ether, 35 mL, 0.11 mol). After stirring at 0° C. for 2 h, the reaction was quenched with MeOH (5 mL) and 2 M hydrochloric acid (50 mL). The volatile materials were removed by concentrating on a rotary evaporator and the residue partitioned between saturated ammonium chloride (200 mL) and ether (200 mL). The organic layer was separated, and the aqueous layer was extracted with ether (2×200 mL). The combined organic extracts were dried over anhydrous MgSO4, filtered and concentrated to dryness to give the title compoun, which was used without further purification. 1H NMR (500 MHz, CD3OD): δ 7.45-7.02 (m, 9H), 4.08 (dd, 1H), 3.34 (dd, 1H), 2.90 (dd, 1H), 2.03 (s, 3H). the reaction was quenched with MeOH (5 mL) and 2 M hydrochloric acid (50 mL) The volatile materials were removed by concentrating on a rotary evaporator the residue partitioned between saturated ammonium chloride (200 mL) and ether (200 mL) The organic layer was separated the aqueous layer was extracted with ether (2×200 mL) The combined organic extracts were dried over anhydrous MgSO4 filtered concentrated to dryness to give the title compoun, which was used without further purification
Source ID: ord-5db84daac83745bc9e95333aec4e0c20Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 4-(4-chlorophenyl)-3-phenyl-2-butanone (Step D, 13 g, 50 mmol) in MeOH (100 mL) at 0° C. was added sodium borohydride (3.8 g, 100 mmol). After stirring at 0° C. for 30 min, the reaction was quenched by addition of 2 M hydrochloric acid (50 mL). The volatile materials were removed by concentrating on a rotary evaporator and the residue partitioned between water (100 mL) and EtOAc (200 mL). The organic layer was separated and the aqueous layer extracted with EtOAc (2×200 mL). The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to dryness to give the crude product, which was purified by flash column chromatography on silica gel eluted with 10% EtOAc in hexane to afford the pure faster eluting isomer and a mixture containing both the faster eluting isomer and the slower eluting isomer. Faster eluting isomer: 1H NMR (500 MHz, CD3OD): δ 7.25-7.00 (m, 9H), 4.00 (m, 1H), 3.15 (m, 1H), 2.97 (m, 1H), 2.85 (m, 1H), 1.10 (d, 3H). the reaction was quenched by addition of 2 M hydrochloric acid (50 mL) The volatile materials were removed by concentrating on a rotary evaporator the residue partitioned between water (100 mL) and EtOAc (200 mL) The organic layer was separated the aqueous layer extracted with EtOAc (2×200 mL) The combined organic extracts were washed with brine dried over anhydrous sodium sulfate filtered concentrated to dryness
Source ID: ord-2f70beb27aff45bd805b5d885df38187Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 4-(4-chlorophenyl)-3-phenyl-2-butanone (Step D, 13 g, 50 mmol) in MeOH (100 mL) at 0° C. was added sodium borohydride (3.8 g, 100 mmol). After stirring at 0° C. for 30 min, the reaction was quenched by addition of 2 M hydrochloric acid (50 mL). The volatile materials were removed by concentrating on a rotary evaporator and the residue partitioned between water (100 mL) and EtOAc (200 mL). The organic layer was separated and the aqueous layer extracted with EtOAc (2×200 mL). The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to dryness to give the crude product, which was purified by flash column chromatography on silica gel eluted with 10% EtOAc in hexane to afford the pure faster eluting isomer and a mixture containing both the faster eluting isomer and the slower eluting isomer. Faster eluting isomer: 1H NMR (500 MHz, CD3OD): δ 7.25-7.00 (m, 9H), 4.00 (m, 1H), 3.15 (m, 1H), 2.97 (m, 1H), 2.85 (m, 1H), 1.10 (d, 3H). the reaction was quenched by addition of 2 M hydrochloric acid (50 mL) The volatile materials were removed by concentrating on a rotary evaporator the residue partitioned between water (100 mL) and EtOAc (200 mL) The organic layer was separated the aqueous layer extracted with EtOAc (2×200 mL) The combined organic extracts were washed with brine dried over anhydrous sodium sulfate filtered concentrated to dryness
Source ID: ord-050d917513174e70ad5254fe4a126c7aConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of N-methoxy-N-methyl-3-(4-chlorophenyl)-2-phenylpropanamide (Step C, 16 g, 53 mmol, dried by azeotroping with toluene) in anhydrous THF (200 mL) at 0° C. was added methylmagnesium bromide (3 M in ether, 35 mL, 0.11 mol). After stirring at 0° C. for 2 h, the reaction was quenched with MeOH (5 mL) and 2 M hydrochloric acid (50 mL). The volatile materials were removed by concentrating on a rotary evaporator and the residue partitioned between saturated ammonium chloride (200 mL) and ether (200 mL). The organic layer was separated, and the aqueous layer was extracted with ether (2×200 mL). The combined organic extracts were dried over anhydrous MgSO4, filtered and concentrated to dryness to give the title compound, which was used without further purification. 1H NMR (500 MHz, CD3OD): δ 7.45-7.02 (m, 9H), 4.08 (dd, 1H), 3.34 (dd, 1H), 2.90 (dd, 1H), 2.03 (s, 3H). the reaction was quenched with MeOH (5 mL) and 2 M hydrochloric acid (50 mL) The volatile materials were removed by concentrating on a rotary evaporator the residue partitioned between saturated ammonium chloride (200 mL) and ether (200 mL) The organic layer was separated the aqueous layer was extracted with ether (2×200 mL) The combined organic extracts were dried over anhydrous MgSO4 filtered concentrated to dryness
Source ID: ord-c60e81e8d7aa47b4b36386892baca9dbConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 4-(4-chlorophenyl)-3-phenyl-2-butanone (Step D, 13 g, 50 mmol) in methanol (100 mL) at 0° C. was added sodium borohydride (3.8 g, 100 mmol). After stirring at 0° C. for 30 min, the reaction was quenched by adding 2 M hydrochloric acid (50 mL). The volatile materials were removed by concentrating on a rotary evaporator and the residue partitioned between water (100 mL) and ethyl acetate (200 mL). The organic layer was separated and the aqueous layer extracted with ethyl acetate (2×200 mL) The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to dryness to give the crude product, which was purified by flash column chromatography on silica gel eluted with 10% ethyl acetate in hexane to afford the pure faster eluting isomer and a mixture containing both the faster eluting isomer and the slower eluting isomer. Faster eluting isomer: 1H NMR (500 MHz, CD3OD): δ 7.25-7.00 (m, 9H), 4.00 (m, 1H), 3.15 (m, 1H), 2.97 (m, 1H), 2.85 (m, 1H), 1.10 (d, 3H). the reaction was quenched by adding 2 M hydrochloric acid (50 mL) The volatile materials were removed by concentrating on a rotary evaporator the residue partitioned between water (100 mL) and ethyl acetate (200 mL) The organic layer was separated the aqueous layer extracted with ethyl acetate (2×200 mL) The combined organic extracts were washed with brine dried over anhydrous sodium sulfate filtered concentrated to dryness
Source ID: ord-c37e887558f2490c9a6355bc2db8c923Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of N-methoxy-N-methyl-3-(4-chlorophenyl)-2-phenylpropanamide (Step C, 16 g, 53 mmol, dried by azeotroping with toluene) in anhydrous tetrahydrofuran (200 mL) at 0° C. was added methylmagnesium bromide (3 M in ether, 35 mL, 0.11 mol). After stirring at 0° C. for 2 h, the reaction was quenched with methanol (5 mL) and 2 M hydrochloric acid (50 mL). The volatile materials were removed by concentrating on a rotary evaporator and the residue partitioned between saturated ammonium chloride (200 mL) and ether (200 mL). The organic layer was separated, and the aqueous layer was extracted with ether (2 times 200 mL) The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated to dryness to give the title compound, which was used without further purification. 1H NMR (500 MHz, CD3OD): δ 7.45-7.02 (m, 9H), 4.08 (dd, 1H), 3.34 (dd, 1H), 2.90 (dd, 1H), 2.03 (s, 3H). the reaction was quenched with methanol (5 mL) and 2 M hydrochloric acid (50 mL) The volatile materials were removed by concentrating on a rotary evaporator the residue partitioned between saturated ammonium chloride (200 mL) and ether (200 mL) The organic layer was separated the aqueous layer was extracted with ether (2 times 200 mL) The combined organic extracts were dried over anhydrous magnesium sulfate filtered concentrated to dryness
Source ID: ord-1a79674f4b4046609a32827825f8e001Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 4-(4-chlorophenyl)-3-phenyl-2-butanone (Step D, 13 g, 50 mmol) in MeOH (100 mL) at 0° C. was added sodium borohydride (3.8 g, 100 mmol). After stirring at 0° C. for 30 min, the reaction was quenched by addition of 2 M hydrochloric acid (50 mL). The volatile materials were removed by concentrating on a rotary evaporator and the residue partitioned between water (100 mL) and EtOAc (200 mL). The organic layer was separated and the aqueous layer extracted with EtOAc (2×200 mL). The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to dryness to give the crude product, which was purified by flash column chromatography on silica gel eluted with 10% EtOAc in hexane to afford the pure faster eluting isomer and a mixture containing both the faster eluting isomer and the slower eluting isomer. Faster eluting isomer: 1H NMR (500 MHz, CD3OD): δ 7.25-7.00 (m, 9H), 4.00 (m, 1H), 3.15 (m, 1H), 2.97 (m, 1H), 2.85 (m, 1H), 1.10 (d, 3H). the reaction was quenched by addition of 2 M hydrochloric acid (50 mL) The volatile materials were removed by concentrating on a rotary evaporator the residue partitioned between water (100 mL) and EtOAc (200 mL) The organic layer was separated the aqueous layer extracted with EtOAc (2×200 mL) The combined organic extracts were washed with brine dried over anhydrous sodium sulfate filtered concentrated to dryness
Source ID: ord-050d917513174e70ad5254fe4a126c7aConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of N-methoxy-N-methyl-3-(4-chlorophenyl)-2-phenylpropanamide (Step C, 16 g, 53 mmol, dried by azeotroping with toluene) in anhydrous THF (200 mL) at 0° C. was added methylmagnesium bromide (3 M in ether, 35 mL, 0.11 mol). After stirring at 0° C. for 2 h, the reaction was quenched with MeOH (5 mL) and 2 M hydrochloric acid (50 mL). The volatile materials were removed by concentrating on a rotary evaporator and the residue partitioned between saturated ammonium chloride (200 mL) and ether (200 mL). The organic layer was separated, and the aqueous layer was extracted with ether (2×200 mL). The combined organic extracts were dried over anhydrous MgSO4, filtered and concentrated to dryness to give the title compound, which was used without further purification. 1H NMR (500 MHz, CD3OD): δ 7.45-7.02 (m, 9H), 4.08 (dd, 1H), 3.34 (dd, 1H), 2.90 (dd, 1H), 2.03 (s, 3H). the reaction was quenched with MeOH (5 mL) and 2 M hydrochloric acid (50 mL) The volatile materials were removed by concentrating on a rotary evaporator the residue partitioned between saturated ammonium chloride (200 mL) and ether (200 mL) The organic layer was separated the aqueous layer was extracted with ether (2×200 mL) The combined organic extracts were dried over anhydrous MgSO4 filtered concentrated to dryness
Source ID: ord-c60e81e8d7aa47b4b36386892baca9dbConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-281993cdaa9a48bf80c747150d6bc2c0Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 4-(4-chlorophenyl)-3-phenyl-2-butanone (Step D, 13 g, 50 mmol) in methanol (100 mL) at 0° C. was added sodium borohydride (3.8 g, 100 mmol). After stirring at 0° C. for 30 min, the reaction was quenched by adding 2 M hydrochloric acid (50 mL). The volatile materials were removed by concentrating on a rotary evaporator and the residue partitioned between water (100 mL) and ethyl acetate (200 mL). The organic layer was separated and the aqueous layer extracted with ethyl acetate (2×200 mL) The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to dryness to give the crude product, which was purified by flash column chromatography on silica gel eluted with 10% ethyl acetate in hexane to afford the pure faster eluting isomer and a mixture containing both the faster eluting isomer and the slower eluting isomer. Faster eluting isomer: 1H NMR (500 MHz, CD3OD): δ 7.25-7.00 (m, 9H), 4.00 (m, 1H), 3.15 (m, 1H), 2.97 (m, 1H), 2.85 (m, 1H), 1.10 (d, 3H). the reaction was quenched by adding 2 M hydrochloric acid (50 mL) The volatile materials were removed by concentrating on a rotary evaporator the residue partitioned between water (100 mL) and ethyl acetate (200 mL) The organic layer was separated the aqueous layer extracted with ethyl acetate (2×200 mL) The combined organic extracts were washed with brine dried over anhydrous sodium sulfate filtered concentrated to dryness
Source ID: ord-c37e887558f2490c9a6355bc2db8c923PubChem References
These sources are listed in the compound's public database record.
Request a Quote
Send the required specification, quantity, destination and intended use. The CATO team will review availability and respond.