No renderable structure data available
C=CCOC1=CC=CC(=C1)OChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 3-prop-2-enoxyphenol |
|---|---|
| IUPAC Name | — |
| CAS Number | 1616-51-9 |
| Database ID | 5314152 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
3-prop-2-enoxyphenol (CAS 1616-51-9) 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 5314152
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-9863e0716c3440789d726e8c86e8ffafConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 3-allyloxyphenol (1.19 g), 2-bromoacetophenone (1.0 g) and potassium carbonate (1.10 g) in 2-butanone (15 ml) was refluxed for four hours. The mixture was partioned between 0.2N HCl and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, concentrated in vacuo. Column Chromatography (silica gel 60, 50% methylene chloride in hexane) gave the title compound. The organic layer was dried over magnesium sulfate filtered concentrated in vacuo
Source ID: ord-068d28c25dbf4c56bf68a52145af0b7aConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Diethyl azodicarboxylate (26.1 g, 0.15 mol) and triphenyl phosphine (39.3 g, 0.15 mol) were added to a solution of 3-allyloxyphenol (15 g, 0.1 mol) and 3,4-dimethoxycinnamyl alcohol (19.4 g, 0.1 mol) in THF (100 ml). The mixture was stirred at room temperature overnight, and ethyl ether was added. The precipitate was filtered off, and the filtrate was evaporated to a residue, which was purified by HPLC using hexane-ethyl acetate (4:1 v/v) as a liquid phase. 3,4-Dimethoxycinnamyl allyloxyphenyl ether was isolated as a crystalline mass (7.4 g, 23%), m.p. 60°-60.5° C.; NMR (CDCl3): δ3.93, 3.94 (s, s, 2 OCH3), 4.57 (d, t, J=5.5, 1.5, 1.5 Hz, CH2CH=CH2), 4.71 (d, d, J=6.0, 1.5 Hz, CH=CHCH2), 5.28-5.50 (m, CH2CH=CH2), 6.10 (m, CH2CH=CH2 ), 6.26-6.40 (m, CH=CHCH2), 6.56-7.28 (m, ArH). The precipitate was filtered off the filtrate was evaporated to a residue, which was purified by HPLC
Source ID: ord-ff9d07b89b0e49219a15a5da3d5d6512Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Diethyl azodicarboxylate (26.1 g, 0.15 mol) and triphenyl phosphine (39.3 g, 0.15 mol) were added to a solution of 3-allyloxyphenol (15 g, 0.1 mol) and 3,4-dimethoxycinnamyl alcohol (19.4 g, 0.1 mol) in THF (100 ml). The mixture was stirred at room temperature overnight, and ethyl ether was added. The precipitate was filtered off, and the filtrate was evaporated to a residue, which was purified by HPLC using hexane-ethyl acetate (4:1 v/v) as a liquid phase. 3,4-Dimethoxycinnamyl allyloxyphenyl ether was isolated as a crystalline mass (7.4 g, 23%), m.p. 60°-60.5° C.; NMR (CDCl3): δ3.93, 3.94 (s, s, 2 OCH3), 4.57 (d, t, J=5.5, 1.5, 1.5 Hz, CH2CH=CH2), 4.71 (d, d, J=6.0, 1.5 Hz, CH=CHCH2), 5.28-5.50 (m, CH2CH=CH2), 6.10 (m, CH2CH=CH2 ), 6.26-6.40 (m, CH=CHCH2), 6.56-7.28 (m, ArH). The precipitate was filtered off the filtrate was evaporated to a residue, which was purified by HPLC
Source ID: ord-ff9d07b89b0e49219a15a5da3d5d6512Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of resorcinol (40 g, 0.4 mol) and allyl bromide (32 g, 0.26 mol) in acetone (500 ml) containing potassium carbonate (55 g, 0.4 mol) was heated, with stirring, under reflux for 10 hours. The mixture was filtered, and the filtrate was evaporated to dryness. The residue was purified by means of PrepPak 500/silica on a Waters Associates Prep LC/System 500 at 250 ml/min using hexane-ethyl acetate (8:1, v/v) as a liquid phase. 3-Allyloxyphenol was isolated as a colorless oil (20 g, 51% based on ally bromide); NMR (chloroform-d): δ4.78 (s, OH), 4.55 (d, J=5.5 Hz, CH2CH=CH2), 5.29-5.50 (m, CH2CH=CH2), 6.07 (m, CH2CH=CH2), 7.18 (t, J=8.5 Hz, H-5), 6.46-6.58 (m, remaining Ar--H). was heated under reflux for 10 hours The mixture was filtered the filtrate was evaporated to dryness The residue was purified by means of PrepPak 500/silica on a Waters Associates Prep LC/System 500 at 250 ml/min
Source ID: ord-36d047b974804750968f713207bb05eeConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of resorcinol (40 g, 0.4 mol) and allyl bromide (32 g, 0.26 mol) in acetone (500 ml) containing potassium carbonate (55 g, 0.4 mol) was heated, with stirring, under reflux for 10 hours. The mixture was filtered, and the filtrate was evaporated to dryness. The residue was purified by means of PrepPak 500/silica on a Waters Associates Prep LC/System 500 at 250 ml/min using hexane-ethyl acetate (8:1, v/v) as a liquid phase. 3-Allyloxyphenol was isolated as a colorless oil (20 g, 51% based on ally bromide); NMR (chloroform-d): δ4.78 (s, OH), 4.55 (d, J=5.5 Hz, CH2CH=CH2), 5.29-5.50 (m, CH2CH=CH2), 6.07 (m, CH2CH=CH2), 7.18 (t, J=8.5 Hz, H-5), 6.46-6.58 (m, remaining Ar--H). was heated under reflux for 10 hours The mixture was filtered the filtrate was evaporated to dryness The residue was purified by means of PrepPak 500/silica on a Waters Associates Prep LC/System 500 at 250 ml/min
Source ID: ord-36d047b974804750968f713207bb05eeConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 3-allyloxyphenol (1.19 g), 2-bromoacetophenone (1.0 g) and potassium carbonate (1.10 g) in 2-butanone (15 ml) was refluxed for four hours. The mixture was partioned between 0.2N HCl and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, concentrated in vacuo. Column Chromatography (silica gel 60, 50% methylene chloride in hexane) gave the title compound. The organic layer was dried over magnesium sulfate filtered concentrated in vacuo
Source ID: ord-068d28c25dbf4c56bf68a52145af0b7aConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 3-allyloxyphenol (1.19 g), 2-bromoacetophenone (1.0 g) and potassium carbonate (1.10 g) in 2-butanone (15 ml) was refluxed for four hours. The mixture was partioned between 0.2N HCl and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, concentrated in vacuo. Column Chromatography (silica gel 60, 50% methylene chloride in hexane) gave the title compound. The organic layer was dried over magnesium sulfate filtered concentrated in vacuo
Source ID: ord-068d28c25dbf4c56bf68a52145af0b7aConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Diethyl azodicarboxylate (26.1 g, 0.15 mol) and triphenyl phosphine (39.3 g, 0.15 mol) were added to a solution of 3-allyloxyphenol (15 g, 0.1 mol) and 3,4-dimethoxycinnamyl alcohol (19.4 g, 0.1 mol) in THF (100 ml). The mixture was stirred at room temperature overnight, and ethyl ether was added. The precipitate was filtered off, and the filtrate was evaporated to a residue, which was purified by HPLC using hexane-ethyl acetate (4:1 v/v) as a liquid phase. 3,4-Dimethoxycinnamyl allyloxyphenyl ether was isolated as a crystalline mass (7.4 g, 23%), m.p. 60°-60.5° C.; NMR (CDCl3): δ3.93, 3.94 (s, s, 2 OCH3), 4.57 (d, t, J=5.5, 1.5, 1.5 Hz, CH2CH=CH2), 4.71 (d, d, J=6.0, 1.5 Hz, CH=CHCH2), 5.28-5.50 (m, CH2CH=CH2), 6.10 (m, CH2CH=CH2 ), 6.26-6.40 (m, CH=CHCH2), 6.56-7.28 (m, ArH). The precipitate was filtered off the filtrate was evaporated to a residue, which was purified by HPLC
Source ID: ord-ff9d07b89b0e49219a15a5da3d5d6512Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of resorcinol (40 g, 0.4 mol) and allyl bromide (32 g, 0.26 mol) in acetone (500 ml) containing potassium carbonate (55 g, 0.4 mol) was heated, with stirring, under reflux for 10 hours. The mixture was filtered, and the filtrate was evaporated to dryness. The residue was purified by means of PrepPak 500/silica on a Waters Associates Prep LC/System 500 at 250 ml/min using hexane-ethyl acetate (8:1, v/v) as a liquid phase. 3-Allyloxyphenol was isolated as a colorless oil (20 g, 51% based on ally bromide); NMR (chloroform-d): δ4.78 (s, OH), 4.55 (d, J=5.5 Hz, CH2CH=CH2), 5.29-5.50 (m, CH2CH=CH2), 6.07 (m, CH2CH=CH2), 7.18 (t, J=8.5 Hz, H-5), 6.46-6.58 (m, remaining Ar--H). was heated under reflux for 10 hours The mixture was filtered the filtrate was evaporated to dryness The residue was purified by means of PrepPak 500/silica on a Waters Associates Prep LC/System 500 at 250 ml/min
Source ID: ord-36d047b974804750968f713207bb05eeConditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The crude product from Example 61B in anhydrous DMF (40 mL) was treated with K2CO3 (15.5 g, 112 mmoles) and 4-fluorobenzaldehyde (4.82 mL, 44.9 mmoles). The reaction mixture was stirred overnight at 100° C. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate. The mixture was washed with H2O (2×), brine, dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, 8% ethyl acetate:hexanes) to provide the title compound (5.75 g, 60%). After cooling to room temperature The mixture was washed with H2O (2×), brine dried (Na2SO4) filtered the filtrate concentrated under reduced pressure The residue was purified by flash chromatography (silica gel, 8% ethyl acetate:hexanes)
Source ID: ord-f00f316953c0490bb1351c39a64d504aConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The product from Example 61A (7.19 g, 37.4 mmoles) in THF (30 mL) was treated with 4N NaOH (19 mL, 75 mmoles) and MeOH (5 mL). After one hour, the reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed with aqueous NH4Cl, brine, dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure to provide the title compound without further purification. the reaction mixture was concentrated under reduced pressure The residue was dissolved in ethyl acetate washed with aqueous NH4Cl, brine dried (Na2SO4) filtered the filtrate concentrated under reduced pressure
Source ID: ord-83b92bd422474d3b90f45bf086b1dfbfPubChem References
These sources are listed in the compound's public database record.
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