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CC(=O)CCOCC1=CC=CC=C1Chemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 4-phenylmethoxybutan-2-one |
|---|---|
| IUPAC Name | — |
| CAS Number | 6278-91-7 |
| Database ID | 234511 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
4-phenylmethoxybutan-2-one (CAS 6278-91-7) 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 234511
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-25466980b3774efb9f3f8e72a279076eConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-ccff4359d06845e09fc4c5f02fddb266Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Diisopropylamine (1.23 g, 12.2 mmole) was dissolved in 150 ml dry THF and the reaction was cooled to 0° C. n-Butyllithium (2.5 ml in Hexane, 4.5 ml, 11.2 mmole) was added and the reaction was stirred at 0° C. for 10 minutes. The reaction was cooled to −100° C. and 4-benzyloxy-2-butanone (1.83 g, 10.3 mmole) in 50 ml dry THF (pre-cooled to −78° C.) was added. The reaction was stirred for 30 minutes at −78° C. 4-(4-Chloro-benzenesulfonyl)-5,8-difluoro-2H-chromene (3.2 g, 9.36 mmole) in 20 ml THF (pre-cooled to −78° C.) was added. The reaction was stirred at −78° C. for 1 hour. 20 ml water was added at −78° C. to quench the reaction. After the reaction was warmed up to room temperature, 200 ml EtOAc was added. The organic layer was washed with brine (2×100 ml), dried over Na2SO4 and concentrated. The product was purified by column chromatography (EtOAc/hexane from 0/100 to 40/60 in 45 minute). Yield, 2.6 g, 53%. 1H NMR (CDCl3 400 MHz δ 7.82 (d, J=8.8 Hz, 2H), 7.54 (d, J=8.1 Hz, 2H), 7.20-7.35 (m, 5H), 7.05 (m, 1H), 6.47 (m, 1H), 4.89 (dd, J=11.7 and 2.9 Hz, 1H), 4.42 (s, 3H), 4.24 (dt, J=12.4 and 2.2 Hz, 1H), 3.65 (t, J=5.9 Hz, 2H), 3.31 (m, 1H), 2.33-2.67 (m, 4H). was added The reaction was cooled to −100° C. The reaction was stirred for 30 minutes at −78° C The reaction was stirred at −78° C. for 1 hour to quench the reaction After the reaction was warmed up to room temperature The organic layer was washed with brine (2×100 ml) dried over Na2SO4 concentrated The product was purified by column chromatography (EtOAc/hexane from 0/100 to 40/60 in 45 minute) Yield
Source ID: ord-66349404302045aebad9adf57895975dConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Diisopropylamine (1.23 g, 12.2 mmole) was dissolved in 150 ml dry THF and the reaction was cooled to 0° C. n-Butyllithium (2.5 ml in Hexane, 4.5 ml, 11.2 mmole) was added and the reaction was stirred at 0° C. for 10 minutes. The reaction was cooled to −100° C. and 4-benzyloxy-2-butanone (1.83 g, 10.3 mmole) in 50 ml dry THF (pre-cooled to −78° C.) was added. The reaction was stirred for 30 minutes at −78° C. 4-(4-Chloro-benzenesulfonyl)-5,8-difluoro-2H-chromene (3.2 g, 9.36 mmole) in 20 ml THF (pre-cooled to −78° C.) was added. The reaction was stirred at −78° C. for 1 hour. 20 ml water was added at −78° C. to quench the reaction. After the reaction was warmed up to room temperature, 200 ml EtOAc was added. The organic layer washed with brine (2×100 ml), dried over Na2SO4 and concentrated. The product was purified by column chromatography (EtOAc/hexane from 0/100 to 40/60 in 45 minute). Yield, 2.6 g, 53%. 1H NMR (CDCl3 400 MHz δ 7.82 (d, J=8.8 Hz, 2H), 7.54 (d, J=8.1 Hz, 2H), 7.20-7.35 (m, 5H), 7.05 (m, 1H), 6.47 (m, 1H), 4.89 (dd, J=11.7 and 2.9 Hz, 1H), 4.42 (s, 3H), 4.24 (dt, J=12.4 and 2.2 Hz, 1H), 3.65 (t, J=5.9 Hz, 2H), 3.31 (m, 1H), 2.33-2.67 (m, 4H). was added The reaction was cooled to −100° C. The reaction was stirred for 30 minutes at −78° C The reaction was stirred at −78° C. for 1 hour to quench the reaction After the reaction was warmed up to room temperature The organic layer washed with brine (2×100 ml) dried over Na2SO4 concentrated The product was purified by column chromatography (EtOAc/hexane from 0/100 to 40/60 in 45 minute) Yield
Source ID: ord-49058df9a06c4822a65559889913bc09Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 4-benzyloxy-2-butanone (10 g, 56.1 mmol), ethylene glycol (40 ml, 718 mmol), triethyl orthoformate (9.3 ml, 55.9 mmol) and p-toluenesulfonic acid monohydrate (290 mg, 1.52 mmol) was stirred at room temperature for 13.5 hours. To the reaction mixture, a saturated aqueous sodium hydrogen carbonate solution (40 ml) was added and the mixture was extracted three times with chloroform (50 ml). The organic layer was dried over anhydrous sodium sulfate and concentrated. The crude product was purified by silica gel column chromatography (NH silica gel, elution solvent: heptane/ethyl acetate=1/0 to 4/1 gradient). Desired fractions were concentrated to obtain the title compound (10.08 g, 80.8% yield) as a colorless oil. the mixture was extracted three times with chloroform (50 ml) The organic layer was dried over anhydrous sodium sulfate concentrated The crude product was purified by silica gel column chromatography (NH silica gel, elution solvent: heptane/ethyl acetate=1/0 to 4/1 gradient) Desired fractions were concentrated
Source ID: ord-4bc513ce0dfc42259687f0217e5bcc1dConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-25466980b3774efb9f3f8e72a279076eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 4-benzyloxy-2-butanone (10 g, 56.1 mmol), ethylene glycol (40 ml, 718 mmol), triethyl orthoformate (9.3 ml, 55.9 mmol) and p-toluenesulfonic acid monohydrate (290 mg, 1.52 mmol) was stirred at room temperature for 13.5 hours. To the reaction mixture, a saturated aqueous sodium hydrogen carbonate solution (40 ml) was added and the mixture was extracted three times with chloroform (50 ml). The organic layer was dried over anhydrous sodium sulfate and concentrated. The crude product was purified by silica gel column chromatography (NH silica gel, elution solvent: heptane/ethyl acetate=1/0 to 4/1 gradient). Desired fractions were concentrated to obtain the title compound (10.08 g, 80.8% yield) as a colorless oil. the mixture was extracted three times with chloroform (50 ml) The organic layer was dried over anhydrous sodium sulfate concentrated The crude product was purified by silica gel column chromatography (NH silica gel, elution solvent: heptane/ethyl acetate=1/0 to 4/1 gradient) Desired fractions were concentrated
Source ID: ord-4bc513ce0dfc42259687f0217e5bcc1dConditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 6.37 g (119.1 mmol) of ammonium chloride (dissolved in 15 ml of warm water) and 9 ml (216.6 mmol) of conc. ammonia in water were added to 5.31 g (108.3 mmol) of sodium cyanide in 10 ml of water. 19.3 g (108.3 mmol) of 4-(benzyloxy)butan-2-one, dissolved in 3 ml of ethanol, were then added. The mixture was stirred at RT for 15 min and at 60° C. for 2 h. Another 4 g (81.6 mmol) of sodium cyanide, 4.8 g (89.7 mmol) of ammonium chloride and 6.5 ml (156.4 mmol) of conc. ammonia in water were added and the mixture was stirred at 60° C. for a further 2 h. The reaction solution was then cooled, and 300 ml each of methylenechloride and water were added. After phase separation, the aqueous phase was extracted with 300 ml of methylene chloride. The combined organic phases were dried and concentrated. The crude product was purified on silica gel (cyclohexane/ethyl acetate gradient 6/4-1/1). This gave 19.9 g of the target compound (77% pure, 69% of theory). were then added the mixture was stirred at 60° C. for a further 2 h The reaction solution was then cooled After phase separation the aqueous phase was extracted with 300 ml of methylene chloride The combined organic phases were dried concentrated The crude product was purified on silica gel (cyclohexane/ethyl acetate gradient 6/4-1/1)
Source ID: ord-a89c3f736d854f34ab8c14717e35d666Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 6.37 g (119.1 mmol) of ammonium chloride (dissolved in 15 ml of warm water) and 9 ml (216.6 mmol) of conc. ammonia in water were added to 5.31 g (108.3 mmol) of sodium cyanide in 10 ml of water. 19.3 g (108.3 mmol) of 4-(benzyloxy)butan-2-one, dissolved in 3 ml of ethanol, were then added. The mixture was stirred at RT for 15 min and at 60° C. for 2 h. Another 4 g (81.6 mmol) of sodium cyanide, 4.8 g (89.7 mmol) of ammonium chloride and 6.5 ml (156.4 mmol) of conc. ammonia in water were added and the mixture was stirred at 60° C. for a further 2 h. The reaction solution was then cooled, and 300 ml each of methylenechloride and water were added. After phase separation, the aqueous phase was extracted with 300 ml of methylene chloride. The combined organic phases were dried and concentrated. The crude product was purified on silica gel (cyclohexane/ethyl acetate gradient 6/4-1/1). This gave 19.9 g of the target compound (77% pure, 69% of theory). were then added the mixture was stirred at 60° C. for a further 2 h The reaction solution was then cooled After phase separation the aqueous phase was extracted with 300 ml of methylene chloride The combined organic phases were dried concentrated The crude product was purified on silica gel (cyclohexane/ethyl acetate gradient 6/4-1/1)
Source ID: ord-a89c3f736d854f34ab8c14717e35d666Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 6.37 g (119.1 mmol) of ammonium chloride (dissolved in 15 ml of warm water) and 9 ml (216.6 mmol) of conc. ammonia in water were added to 5.31 g (108.3 mmol) of sodium cyanide in 10 ml of water. 19.3 g (108.3 mmol) of 4-(benzyloxy)butan-2-one, dissolved in 3 ml of ethanol, were then added. The mixture was stirred at RT for 15 min and at 60° C. for 2 h. Another 4 g (81.6 mmol) of sodium cyanide, 4.8 g (89.7 mmol) of ammonium chloride and 6.5 ml (156.4 mmol) of conc. ammonia in water were added and the mixture was stirred at 60° C. for a further 2 h. The reaction solution was then cooled, and 300 ml each of methylenechloride and water were added. After phase separation, the aqueous phase was extracted with 300 ml of methylene chloride. The combined organic phases were dried and concentrated. The crude product was purified on silica gel (cyclohexane/ethyl acetate gradient 6/4-1/1). This gave 19.9 g of the target compound (77% pure, 69% of theory). were then added the mixture was stirred at 60° C. for a further 2 h The reaction solution was then cooled After phase separation the aqueous phase was extracted with 300 ml of methylene chloride The combined organic phases were dried concentrated The crude product was purified on silica gel (cyclohexane/ethyl acetate gradient 6/4-1/1)
Source ID: ord-a89c3f736d854f34ab8c14717e35d666Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Combine 4-benzyloxy-2-butanone (1.78 g, 10 mmol) with 2-amino-1-(4-hydroxy-3-methylsulfinylphenyl)ethanol (10 mmol) in methanol (50 ml) and add sodium cyanoborohydride (0.63 g, 10 mmol). Let stand 16 hours, concentrate the solution and purify the crude product by chromatography on silica gel using chloroform: methanol: ammonium hydroxide (70:27:3) as eluent to obtain the title compound. concentrate the solution purify the crude product by chromatography on silica gel
Source ID: ord-d7b6ee01dd9b48e2b995ab6f3100a7ccConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Combine 4-benzyloxy-2-butanone (2.6 g, 15 mmol) with 5-(2-amino-1-hydroxyethyl)salicylamide (15 mmol in methanol, 50 ml) and treat with sodium cyanoborohydride (0.9 g, 15 mmol). Let stand 16 hours, evaporate the solvent and extract the residue in ethyl acetate/ 1N sodium bicarbonate solution. Separate the organic phase, dry over sodium sulfate and evaporate in vacuo. evaporate the solvent extract the residue in ethyl acetate/ 1N sodium bicarbonate solution Separate the organic phase dry over sodium sulfate evaporate in vacuo
Source ID: ord-e42f7afc30964c418d0f3ed2049021d2PubChem References
These sources are listed in the compound's public database record.
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