No renderable structure data available
C1CCC(C1)C2=CC=CC=C2OChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 2-cyclopentylphenol |
|---|---|
| IUPAC Name | — |
| CAS Number | 1518-84-9 |
| Database ID | 80285 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
2-cyclopentylphenol (CAS 1518-84-9) 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 80285
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 11 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-0701011ad513411b8b94eb73cdf0a9fcConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirring solution of 2-cyclopentyl phenol (7.9 g, 48.7 mmol) in acetic acid (32 mL) and water (16 mL) was added HBr (33% in AcOH, 50.45 mL, 292.2 mmol) followed by the dropwise addition of DMSO (34.8 g, 31.6 mL, 445.0 mmol) over 10 min. The reaction was quenched with saturated aqueous NaHCO3 and concentrated in vacuo to remove gasses. The residue was brought up in ether (200 mL), washed with water (2×100 mL) and brine (100 mL) then dried over Na2SO4. The solution was filtered and concentrated in vacuo to produce an oil which was purified by silica gel chromatography (0-10% ethyl acetate/hexane) to provide 4-bromo-2-cyclopentylphenol (10.5 g, 89% yield) as a colorless oil. 1H NMR (400.0 MHz, DMSO-d6) δ 9.59 (s, 1H), 7.20 (d, J=2.5 Hz, 1H), 7.13 (dd, J=2.5, 8.5 Hz, 1H), 6.73 (d, J=8.5 Hz, 1H), 3.21-3.13 (m, 1H), 1.95-1.88 (m, 2H), 1.77-1.69 (m, 2H), 1.65-1.44 (m, 4H). The reaction was quenched with saturated aqueous NaHCO3 concentrated in vacuo to remove gasses washed with water (2×100 mL) and brine (100 mL) then dried over Na2SO4 The solution was filtered concentrated in vacuo to produce an oil which was purified by silica gel chromatography (0-10% ethyl acetate/hexane)
Source ID: ord-f779f49429f0466d91aeb1029d28b89aConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirring solution of 2-cyclopentyl phenol (7.9 g, 48.7 mmol) in acetic acid (32 mL) and water (16 mL) was added HBr (33% in AcOH, 50.45 mL, 292.2 mmol) followed by the dropwise addition of DMSO (34.8 g, 31.6 mL, 445.0 mmol) over 10 min. The reaction was quenched with saturated aqueous NaHCO3 and concentrated in vacuo to remove gasses. The residue was brought up in ether (200 mL), washed with water (2×100 mL) and brine (100 mL) then dried over Na2SO4. The solution was filtered and concentrated in vacuo to produce an oil which was purified by silica gel chromatography (0-10% ethyl acetate/hexane) to provide 4-bromo-2-cyclopentylphenol (10.5 g, 89% yield) as a colorless oil. 1H NMR (400.0 MHz, DMSO-d6) δ 9.59 (s, 1H), 7.20 (d, J=2.5 Hz, 1H), 7.13 (dd, J=2.5, 8.5 Hz, 1H), 6.73 (d, J=8.5 Hz, 1H), 3.21-3.13 (m, 1H), 1.95-1.88 (m, 2H), 1.77-1.69 (m, 2H), 1.65-1.44 (m, 4H). The reaction was quenched with saturated aqueous NaHCO3 concentrated in vacuo to remove gasses washed with water (2×100 mL) and brine (100 mL) then dried over Na2SO4 The solution was filtered concentrated in vacuo to produce an oil which was purified by silica gel chromatography (0-10% ethyl acetate/hexane)
Source ID: ord-a19eb0a470df42d887d24b124216eed7Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 2-cyclopentyl phenol (3.0 g, 0.0185 mol) was dissolved in CHCl3 (100 mL) and magnetically stirred at room temperature. To this solution was added a solution of Tetrabutyl ammonium tribromide (8.92 g, 0.0185 mol) in CHCl3 (100 mL). The resulting yellow solution was allowed to stir at room temperature for 1 hour. The reaction was quenched with a 5% solution of sodium thiosulfate (200 mL). The biphasic mixture was stirred for 15 min. The organics were separated and concentrated. The residue was dissolved in EtOAc (100 mL) and washed with water (2×100 mL) and brine (1×100 mL). The organics were dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography (silica gel) eluting with 3% EtOAc in Hexanes. The result was a yellow oil (3.70 g). to stir at room temperature for 1 hour The reaction was quenched with a 5% solution of sodium thiosulfate (200 mL) The biphasic mixture was stirred for 15 min The organics were separated concentrated The residue was dissolved in EtOAc (100 mL) washed with water (2×100 mL) and brine (1×100 mL) The organics were dried over Na2SO4 filtered concentrated The residue was purified by flash chromatography (silica gel) eluting with 3% EtOAc in Hexanes
Source ID: ord-c18957ba0b3244828156ce38af5946ccConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 2-cyclopentyl phenol (3.0 g, 0.0185 mol) was dissolved in CHCl3 (100 mL) and magnetically stirred at room temperature. To this solution was added a solution of Tetrabutyl ammonium tribromide (8.92 g, 0.0185 mol) in CHCl3 (100 mL). The resulting yellow solution was allowed to stir at room temperature for 1 hour. The reaction was quenched with a 5% solution of sodium thiosulfate (200 mL). The biphasic mixture was stirred for 15 min. The organics were separated and concentrated. The residue was dissolved in EtOAc (100 mL) and washed with water (2×100 mL) and brine (1×100 mL). The organics were dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography (silica gel) eluting with 3% EtOAc in Hexanes. The result was a yellow oil (3.70 g). to stir at room temperature for 1 hour The reaction was quenched with a 5% solution of sodium thiosulfate (200 mL) The biphasic mixture was stirred for 15 min The organics were separated concentrated The residue was dissolved in EtOAc (100 mL) washed with water (2×100 mL) and brine (1×100 mL) The organics were dried over Na2SO4 filtered concentrated The residue was purified by flash chromatography (silica gel) eluting with 3% EtOAc in Hexanes
Source ID: ord-c18957ba0b3244828156ce38af5946ccConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirring solution of 2-cyclopentyl phenol (7.9 g, 48.7 mmol) in acetic acid (32 mL) and water (16 mL) was added HBr (33% in AcOH, 50.45 mL, 292.2 mmol) followed by the dropwise addition of DMSO (34.8 g, 31.6 mL, 445.0 mmol) over 10 min. The reaction was quenched with saturated aqueous NaHCO3 and concentrated in vacuo to remove gasses. The residue was brought up in ether (200 mL), washed with water (2×100 mL) and brine (100 mL) then dried over Na2SO4. The solution was filtered and concentrated in vacuo to produce an oil which was purified by silica gel chromatography (0-10% ethyl acetate/hexane) to provide 4-bromo-2-cyclopentylphenol (10.5 g, 89% yield) as a colorless oil. 1H NMR (400.0 MHz, DMSO-d6) δ 9.59 (s, 1H), 7.20 (d, J=2.5 Hz, 1H), 7.13 (dd, J=2.5, 8.5 Hz, 1H), 6.73 (d, J=8.5 Hz, 1H), 3.21-3.13 (m, 1H), 1.95-1.88 (m, 2H), 1.77-1.69 (m, 2H), 1.65-1.44 (m, 4H). The reaction was quenched with saturated aqueous NaHCO3 concentrated in vacuo to remove gasses washed with water (2×100 mL) and brine (100 mL) then dried over Na2SO4 The solution was filtered concentrated in vacuo to produce an oil which was purified by silica gel chromatography (0-10% ethyl acetate/hexane)
Source ID: ord-b91f3f1618654556b6293e9a7a827323Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirring solution of 2-cyclopentyl phenol (7.9 g, 48.7 mmol) in acetic acid (32 mL) and water (16 mL) was added HBr (33% in AcOH, 50.45 mL, 292.2 mmol) followed by the dropwise addition of DMSO (34.8 g, 31.6 mL, 445.0 mmol) over 10 min. The reaction was quenched with saturated aqueous NaHCO3 and concentrated in vacuo to remove gasses. The residue was brought up in ether (200 mL), washed with water (2×100 mL) and brine (100 mL) then dried over Na2SO4. The solution was filtered and concentrated in vacuo to produce an oil which was purified by silica gel chromatography (0-10% ethyl acetate/hexane) to provide 4-bromo-2-cyclopentylphenol (10.5 g, 89% yield) as a colorless oil. 1H NMR (400.0 MHz, DMSO-d6) δ 9.59 (s, 1H), 7.20 (d, J=2.5 Hz, 1H), 7.13 (dd, J=2.5, 8.5 Hz, 1H), 6.73 (d, J=8.5 Hz, 1H), 3.21-3.13 (m, 1H), 1.95-1.88 (m, 2H), 1.77-1.69 (m, 2H), 1.65-1.44 (m, 4H). The reaction was quenched with saturated aqueous NaHCO3 concentrated in vacuo to remove gasses washed with water (2×100 mL) and brine (100 mL) then dried over Na2SO4 The solution was filtered concentrated in vacuo to produce an oil which was purified by silica gel chromatography (0-10% ethyl acetate/hexane)
Source ID: ord-f779f49429f0466d91aeb1029d28b89aConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirring solution of 2-cyclopentyl phenol (7.9 g, 48.7 mmol) in acetic acid (32 mL) and water (16 mL) was added HBr (33% in AcOH, 50.45 mL, 292.2 mmol) followed by the dropwise addition of DMSO (34.8 g, 31.6 mL, 445.0 mmol) over 10 min. The reaction was quenched with saturated aqueous NaHCO3 and concentrated in vacuo to remove gasses. The residue was brought up in ether (200 mL), washed with water (2×100 mL) and brine (100 mL) then dried over Na2SO4. The solution was filtered and concentrated in vacuo to produce an oil which was purified by silica gel chromatography (0-10% ethyl acetate/hexane) to provide 4-bromo-2-cyclopentylphenol (10.5 g, 89% yield) as a colorless oil. 1H NMR (400.0 MHz, DMSO-d6) δ 9.59 (s, 1H), 7.20 (d, J=2.5 Hz, 1H), 7.13 (dd, J=2.5, 8.5 Hz, 1H), 6.73 (d, J=8.5 Hz, 1H), 3.21-3.13 (m, 1H), 1.95-1.88 (m, 2H), 1.77-1.69 (m, 2H), 1.65-1.44 (m, 4H). The reaction was quenched with saturated aqueous NaHCO3 concentrated in vacuo to remove gasses washed with water (2×100 mL) and brine (100 mL) then dried over Na2SO4 The solution was filtered concentrated in vacuo to produce an oil which was purified by silica gel chromatography (0-10% ethyl acetate/hexane)
Source ID: ord-571ef9b1e84a400bab8d6ac26b0fff50Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Sulfuryl chloride (0.5 mL) was added dropwise to a solution of methyl 3,5-dibromo-4-mercaptophenylacetate (Preparation E, 0.8 g) in 50 mL of dichloromethane for 1 hour. The sulfenyl chloride product was then added dropwise to an ice-cooled suspension of 2-cyclopentylphenol (0.44 g) and tin (IV) chloride (0.53 mL) in methanol. Following the procedures of Examples 1 and 3, the product methyl 3,5-dibromo-4-(3-cyclopentyl-4-hydroxyphenylsulfonyl)phenylacetate, MP: 171°-173.5° C., (0.7 g) was purified and converted to 3,5-dibromo-4-(3-cyclopentyl-4-hydroxyphenylsulfonyl)phenylacetic acid, MP: 196°-198° C. cooled the product methyl 3,5-dibromo-4-(3-cyclopentyl-4-hydroxyphenylsulfonyl)phenylacetate, MP: 171°-173.5° C., (0.7 g) was purified
Source ID: ord-1f09e4f539b94376bb42999d22300a2bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 486.7 g (3.0 mol) of 2-cyclopentylphenol, 472 g (3.9 mol) of allyl bromide and 830 g (6.0 mol) of potassium carbonate are heated under reflux in 2.5 l of acetone while stirring vigorously for 26 h. The cooled reaction mixture is filtered, and the filtrate is concentrated in vacuo. The residue is taken up in petroleum ether, and the solution is washed three times with 2N sodium hydroxide solution. The organic phase is dried over magnesium sulfate and concentrated in vacuo, and the residue is finally distilled in vacuo. 593 g (97% of theory) of 2-cyclopentylphenyl allyl ether are obtained. The cooled reaction mixture is filtered the filtrate is concentrated in vacuo the solution is washed three times with 2N sodium hydroxide solution The organic phase is dried over magnesium sulfate concentrated in vacuo the residue is finally distilled in vacuo
Source ID: ord-8e094ef3640b4d4484b7d00c6e7e9640Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 2-cyclopentyl phenol (3.0 g, 0.0185 mol) was dissolved in CHCl3 (100 mL) and magnetically stirred at room temperature. To this solution was added a solution of Tetrabutyl ammonium tribromide (8.92 g, 0.0185 mol) in CHCl3 (100 mL). The resulting yellow solution was allowed to stir at room temperature for 1 hour. The reaction was quenched with a 5% solution of sodium thiosulfate (200 mL). The biphasic mixture was stirred for 15 min. The organics were separated and concentrated. The residue was dissolved in EtOAc (100 mL) and washed with water (2×100 mL) and brine (1×100 mL). The organics were dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography (silica gel) eluting with 3% EtOAc in Hexanes. The result was a yellow oil (3.70 g). to stir at room temperature for 1 hour The reaction was quenched with a 5% solution of sodium thiosulfate (200 mL) The biphasic mixture was stirred for 15 min The organics were separated concentrated The residue was dissolved in EtOAc (100 mL) washed with water (2×100 mL) and brine (1×100 mL) The organics were dried over Na2SO4 filtered concentrated The residue was purified by flash chromatography (silica gel) eluting with 3% EtOAc in Hexanes
Source ID: ord-c18957ba0b3244828156ce38af5946ccPubChem References
These sources are listed in the compound's public database record.
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