Reaction #3875336
Related Literature (1)
openreactiondata ↗doi:10.1039/C8SC04228D
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-d8cc9e7b7a4444fb87e77534ff5289acNo renderable structure data available
CCC(=O)CC1=CC=CC=C1Chemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 1-phenylbutan-2-one |
|---|---|
| IUPAC Name | — |
| CAS Number | 1007-32-5 |
| Database ID | 13879 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
1-phenylbutan-2-one (CAS 1007-32-5) 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 13879
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-d8cc9e7b7a4444fb87e77534ff5289acConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-40ea89f36f3a4326b368b593598f9f4aConditions: temp:167.51; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of formic acid (250 ml) and formamide (500 ml) was added 1-phenyl-2-butanone (25 g, 0.168 mols); the reaction was then heated to 165-170° C. for four hours. The reaction was then cooled and poured into water (1 l). The aqueous phase was then extracted with ethyl acetate (3×100 ml). The organic phase was washed with saturated sodium bicarbonate (2×200 ml) and dried over magnesium sulfate. Evaporation of the solvent yielded an oil (24.1 g, 80%). The reaction was then cooled The aqueous phase was then extracted with ethyl acetate (3×100 ml) The organic phase was washed with saturated sodium bicarbonate (2×200 ml) dried over magnesium sulfate Evaporation of the solvent
Source ID: ord-148f40968ba246b7a9b2c710032f4e13Conditions: temp:167.51; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of formic acid (250 ml) and formamide (500 ml) was added 1-phenyl-2-butanone (25 g, 0.168 mols); the reaction was then heated to 165-170° C. for four hours. The reaction was then cooled and poured into water (1 l). The aqueous phase was then extracted with ethyl acetate (3×300 ml). The organic phase was washed with saturated sodium bicarbonate (2×200 ml) and dried over magnesium sulfate. Evaporation of the solvent yielded an oil (24.1 g, 80%). The reaction was then cooled The aqueous phase was then extracted with ethyl acetate (3×300 ml) The organic phase was washed with saturated sodium bicarbonate (2×200 ml) dried over magnesium sulfate Evaporation of the solvent
Source ID: ord-1a59c34be07d459ab977f83207a995efConditions: temp:167.51; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of formic acid (250 ml) and formamide (500 ml) was added 1-phenyl-2-butanone (25 g, 0.168 mols); the reaction was then heated to 165-170° C. for four hours. The reaction was then cooled and poured into water (1 l). The aqueous phase was then extracted with ethyl acetate (3×100 ml). The organic phase was washed with saturated sodium bicarbonate (2×200 ml) and dried over magnesium sulfate. Evaporation of the solvent yielded an oil (24.1 g, 80%). The reaction was then cooled The aqueous phase was then extracted with ethyl acetate (3×100 ml) The organic phase was washed with saturated sodium bicarbonate (2×200 ml) dried over magnesium sulfate Evaporation of the solvent
Source ID: ord-148f40968ba246b7a9b2c710032f4e13Conditions: temp:167.51; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of formic acid (250 ml) and formamide (500 ml) was added 1-phenyl-2-butanone (25 g, 0.168 mols); the reaction was then heated to 165-170° C. for four hours. The reaction was then cooled and poured into water (1 l). The aqueous phase was then extracted with ethyl acetate (3×100 ml). The organic phase was washed with saturated sodium bicarbonate (2×200 ml) and dried over magnesium sulfate. Evaporation of the solvent yielded an oil (24.1 g, 80%). The reaction was then cooled The aqueous phase was then extracted with ethyl acetate (3×100 ml) The organic phase was washed with saturated sodium bicarbonate (2×200 ml) dried over magnesium sulfate Evaporation of the solvent
Source ID: ord-148f40968ba246b7a9b2c710032f4e13Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Ethyl benzyl ketone is reacted with 1-bromo-3-butene according to the foregoing details and there is obtained 5-phenyl-oct-1-en-6-one of boiling point 106° C./4 mmHg; nD20 =1.5088.
Source ID: ord-046350bfbe8b435b90f510627be42cddConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Ethyl benzyl ketone is reacted with crotyl chloride according to the foregoing details and there is obtained 5-phenyl-oct-2-en-6-one of boiling point 95° C./3 mmHg; nD20 =1.5102.
Source ID: ord-c7a2bb7643e24c02bacadd45b9b083e3Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: If ethyl benzyl ketone is reacted with β-methallyl chloride according to the foregoing details, then there is obtained 2-methyl-4-phenyl-hept-1-en-5-one of boiling point 93° C./3 mmHg; nD20 =1.5094.
Source ID: ord-b7fb55c3389d4d68a634c32deee08858Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 192 g (2.4 mol) of 50% sodium hydroxide and 6 g of hexadecyl-trimethylammonium bromide are placed in a 2-liter flask provided with a thermometer, stirrer and reflux condenser and there is then added dropwise while stirring within 0.5 hour a mixture of 296 g (2 mol) of ethyl benzyl ketone and 251 g (2.4 mol) of prenyl chloride. The mixture is warmed to 60° C. and stirred for 3 hours. The mixture is left to cool and 500 ml of ice/water are added thereto. The mixture is extracted four times with ether and washed neutral with water. The phase separation can be facilitated by the addition of a small amount of alcohol. After drying over sodium sulphate, the ether is evaporated and a fractional distillation is then carried out. There are thus obtained 224 g of 2-methyl-5-phenyl-oct-2-en-6-one of boiling point 106° C./3 mmHg; nD20 =1.5092-88; yield 75%. provided with a thermometer, stirrer reflux condenser there is then added dropwise stirred for 3 hours The mixture is left to cool The mixture is extracted four times with ether washed neutral with water The phase separation can be facilitated by the addition of a small amount of alcohol After drying over sodium sulphate the ether is evaporated a fractional distillation
Source ID: ord-373a6d5ca5e642fc87bf3b267873b2a4Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: In a 2-liter flask provided with a thermometer, stirrer, dropping funnel and reflux condenser 600 ml of absolute alcohol are treated portionwise while stirring with 30 g of sodium metal and the mixture is held at reflux temperature until the metal has dissolved. Within 0.5 hour there is added dropwise to the boiling solution a mixture of 117.2 g of benzyl cyanide and 153.2 g of ethyl propionate and the mixture is heated for a further 3 hours. The alcohol is then distilled off and there are added 300 ml of toluene, followed by 250 ml of ice/water. The aqueous phase is separated, washed with 300 ml of toluene and then 540 g of 96% sulphuric acid are added. The mixture is held at reflux temperature until the evolution of carbon dioxide ceases, cooled, diluted with 250 ml of ice/water and extracted with two 300 ml portions of toluene. The toluene extracts are washed with water, with 10% sodium carbonate solution and again with water, dried over sodium sulphate and evaporated. Distillation gives 79 g of ethyl benzyl ketone of boiling point 69° C./3 mmHg; nD20 =1.5109; yield 53%. In a 2-liter flask provided with a thermometer, stirrer are treated portionwise at reflux temperature until the metal has dissolved Within 0.5 hour there is added dropwise to the boiling solution the mixture is heated for a further 3 hours The alcohol is then distilled off there are added 300 ml of toluene The aqueous phase is separated washed with 300 ml of toluene 540 g of 96% sulphuric acid are added at reflux temperature until the evolution of carbon dioxide ceases cooled diluted with 250 ml of ice/water extracted with two 300 ml portions of toluene The toluene extracts are washed with water, with 10% sodium carbonate solution and again with water dried over sodium sulphate evaporated Distillation
Source ID: ord-04dfb8f669644338b85e9f5e690be689Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Ethyl benzyl ketone is reacted with 1-bromo-3-butene according to the foregoing details and there is obtained 5-phenyl-oct-1-en-6-one of boiling point 106° C./4 mmHg; nD20 =1.5088.
Source ID: ord-68c25e6e8855448186f4cee1853821b6PubChem References
These sources are listed in the compound's public database record.
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