No renderable structure data available
C=CCC(COCC1=CC=CC=C1)OChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 1-phenylmethoxypent-4-en-2-ol |
|---|---|
| IUPAC Name | — |
| CAS Number | 58931-16-1 |
| Database ID | 10035478 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
1-phenylmethoxypent-4-en-2-ol (CAS 58931-16-1) 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 10035478
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-ea691aa8f0f94939ae7dd74b31af0544Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: NaH (4.8 g, 120 mmol) was added portion wise to a stirred solution of 1-(benzyloxy)pent-4-en-2-ol (11) (15.3 g, 79.6 mmol) in THF (100 mL) at 0° C. After addition, the mixture was warmed to room temperature and stirred for another hour before it was cooled to 0° C. Allyl bromide (9 mL, 103.5 mmol) was added to the reaction and the resulting mixture was warmed to room temperature and then heated to 50° C. overnight. After cooling to room temperature, the mixture was quenched with saturated NH4Cl and worked up under standard conditions. The residue was purified over silica using Et2O and hexane to give ((2-(allyloxy)pent-4-enyloxy)methyl)benzene (12). After addition was cooled to 0° C the resulting mixture was warmed to room temperature heated to 50° C. overnight After cooling to room temperature the mixture was quenched with saturated NH4Cl The residue was purified over silica
Source ID: ord-f9391ad3f9e24eab9ba4a508c82f6de1Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 2-(Benzyloxy)acetaldehyde (5 g, 33.3 mmol) in dry THF (10 mL) was added dropwise to a stirred and cooled solution of allylmagnesium chloride (25 mL, 2 M in THF, 50 mmol) in THF (100 mL) at −78° C. After the addition, the solution was allowed to warm to 0° C. and quenched with saturated NH4Cl solution. After standard aqueous work up, the residue was purified over silica using EtOAc and hexane to give 1-(benzyloxy)pent-4-en-2-ol (11). After the addition quenched with saturated NH4Cl solution After standard aqueous work up, the residue was purified over silica
Source ID: ord-0b5732e504db4b868c045ef0f3144190Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: NaH (4.8 g, 120 mmol) was added portion wise to a stirred solution of 1-(benzyloxy)pent-4-en-2-ol (11) (15.3 g, 79.6 mmol) in THF (100 mL) at 0° C. After addition, the mixture was warmed to room temperature and stirred for another hour before it was cooled to 0° C. Allyl bromide (9 mL, 103.5 mmol) was added to the reaction and the resulting mixture was warmed to room temperature and then heated to 50° C. overnight. After cooling to room temperature, the mixture was quenched with saturated NH4Cl and worked up under standard conditions. The residue was purified over silica using Et2O and hexane to give ((2-(allyloxy)pent-4-enyloxy)methyl)benzene (12). After addition was cooled to 0° C the resulting mixture was warmed to room temperature heated to 50° C. overnight After cooling to room temperature the mixture was quenched with saturated NH4Cl The residue was purified over silica
Source ID: ord-04e899cb62dd442ca75e4bdf08a97004Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 2-(Benzyloxy)acetaldehyde (5 g, 33.3 mmol) in dry THF (10 mL) was added dropwise to a stirred and cooled solution of allylmagnesium chloride (25 mL, 2 M in THF, 50 mmol) in THF (100 mL) at −78° C. After the addition, the solution was allowed to warm to 0° C. and quenched with saturated NH4Cl solution. After standard aqueous work up, the residue was purified over silica using EtOAc and hexane to give 1-(benzyloxy)pent-4-en-2-ol (11). After the addition quenched with saturated NH4Cl solution After standard aqueous work up, the residue was purified over silica
Source ID: ord-3ee74aae66cb4b86b2365f387402febeConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: NaH (4.8 g, 120 mmol) was added portion wise to a stirred solution of 1-(benzyloxy)pent-4-en-2-ol (11) (15.3 g, 79.6 mmol) in THF (100 mL) at 0° C. After addition, the mixture was warmed to room temperature and stirred for another hour before it was cooled to 0° C. Allyl bromide (9 mL, 103.5 mmol) was added to the reaction and the resulting mixture was warmed to room temperature and then heated to 50° C. overnight. After cooling to room temperature, the mixture was quenched with saturated NH4Cl and worked up under standard conditions. The residue was purified over silica using Et2O and hexane to give ((2-(allyloxy)pent-4-enyloxy)methyl)benzene (12). After addition was cooled to 0° C the resulting mixture was warmed to room temperature heated to 50° C. overnight After cooling to room temperature the mixture was quenched with saturated NH4Cl The residue was purified over silica
Source ID: ord-2024e2e9592e4800895b7c74f9590c15Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: NaH (4.8 g, 120 mmol) was added portion wise to a stirred solution of 1-(benzyloxy)pent-4-en-2-ol (11) (15.3 g, 79.6 mmol) in THF (100 mL) at 0° C. After addition, the mixture was warmed to room temperature and stirred for another hour before it was cooled to 0° C. Allyl bromide (9 mL, 103.5 mmol) was added to the reaction and the resulting mixture was warmed to room temperature and then heated to 50° C. overnight. After cooling to room temperature, the mixture was quenched with saturated NH4Cl and worked up under standard conditions. The residue was purified over silica using Et2O and hexane to give ((2-(allyloxy)pent-4-enyloxy)methyl)benzene (12). After addition was cooled to 0° C the resulting mixture was warmed to room temperature heated to 50° C. overnight After cooling to room temperature the mixture was quenched with saturated NH4Cl The residue was purified over silica
Source ID: ord-2024e2e9592e4800895b7c74f9590c15Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 2-(Benzyloxy)acetaldehyde (5 g, 33.3 mmol) in dry THF (10 mL) was added dropwise to a stirred and cooled solution of allylmagnesium chloride (25 mL, 2 M in THF, 50 mmol) in THF (100 mL) at −78° C. After the addition, the solution was allowed to warm to 0° C. and quenched with saturated NH4Cl solution. After standard aqueous work up, the residue was purified over silica using EtOAc and hexane to give 1-(benzyloxy)pent-4-en-2-ol (11). After the addition quenched with saturated NH4Cl solution After standard aqueous work up, the residue was purified over silica
Source ID: ord-2ecd7da9568442ffabf69095bebf3b14Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: NaH (4.8 g, 120 mmol) was added portion wise to a stirred solution of 1-(benzyloxy)pent-4-en-2-ol (11) (15.3 g, 79.6 mmol) in THF (100 mL) at 0° C. After addition, the mixture was warmed to room temperature and stirred for another hour before it was cooled to 0° C. Allyl bromide (9 mL, 103.5 mmol) was added to the reaction and the resulting mixture was warmed to room temperature and then heated to 50° C. overnight. After cooling to room temperature, the mixture was quenched with saturated NH4Cl and worked up under standard conditions. The residue was purified over silica using Et2O and hexane to give ((2-(allyloxy)pent-4-enyloxy)methyl)benzene (12). After addition was cooled to 0° C the resulting mixture was warmed to room temperature heated to 50° C. overnight After cooling to room temperature the mixture was quenched with saturated NH4Cl The residue was purified over silica
Source ID: ord-f9391ad3f9e24eab9ba4a508c82f6de1Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 2-(Benzyloxy)acetaldehyde (5 g, 33.3 mmol) in dry THF (10 mL) was added dropwise to a stirred and cooled solution of allylmagnesium chloride (25 mL, 2 M in THF, 50 mmol) in THF (100 mL) at −78° C. After the addition, the solution was allowed to warm to 0° C. and quenched with saturated NH4Cl solution. After standard aqueous work up, the residue was purified over silica using EtOAc and hexane to give 1-(benzyloxy)pent-4-en-2-ol (11). After the addition quenched with saturated NH4Cl solution After standard aqueous work up, the residue was purified over silica
Source ID: ord-0b5732e504db4b868c045ef0f3144190Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 2-(Benzyloxy)acetaldehyde (5 g, 33.3 mmol) in dry THF (10 mL) was added dropwise to a stirred and cooled solution of allylmagnesium chloride (25 mL, 2 M in THF, 50 mmol) in THF (100 mL) at −78° C. After the addition, the solution was allowed to warm to 0° C. and quenched with saturated NH4Cl solution. After standard aqueous work up, the residue was purified over silica using EtOAc and hexane to give 1-(benzyloxy)pent-4-en-2-ol (11). After the addition quenched with saturated NH4Cl solution After standard aqueous work up, the residue was purified over silica
Source ID: ord-0b5732e504db4b868c045ef0f3144190Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirring 0° C. solution of 59.0 g of product from Example 1 in 375 ml of diethyl ether is added, dropwise, 432.24 ml of 1M allylmagnesium bromide in ether. The reaction is stirred at 0° C. for 1 hour, followed by overnight stirring at room temperature. The reaction is cooled to 0° C., hydrolyzed with saturated ammonium chloride, and the layers are separated. The organic layer is washed with saturated sodium chloride, dried and concentrated in vacuo to give the product as an oil. The crude oil is purified by Kugelrohr distillation (bath temperature 100° C.) to give 61.5 g of the desired product as a colorless oil. followed by overnight stirring at room temperature the layers are separated The organic layer is washed with saturated sodium chloride dried concentrated in vacuo
Source ID: ord-8d08157a102b4f9c89a6a53c15e800daPubChem References
These sources are listed in the compound's public database record.
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