No renderable structure data available
C1CC(CC=C1)COChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | cyclohex-3-en-1-ylmethanol |
|---|---|
| IUPAC Name | — |
| CAS Number | 1679-51-2 |
| Database ID | 15512 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
cyclohex-3-en-1-ylmethanol (CAS 1679-51-2) 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 15512
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-6b82323527f043f2aebec7422d60477fConditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a mixture of 3-cyclohexene-1-methanol (Aldrich, 13.0 mL, 0.11 mol), N,N-diisopropylethylamine (43 mL, 0.244 mol) and 4-dimethylaminopyridine (2.70 g., 0.022 mol) in 375 mL of dry CH2CI2 under N2 at 25° C. was added tert-butyldiphenylchlorosilane (32 mL, 0.123 mol). The mixture was stirred at 25° C. for 48 hours. The reaction mixture was washed sequentially with 150 mL portions of 1N HCl, water, brine and dried over anhydrous MgSO4. The solvent was evaporated. The residue was loaded onto a 4"×4" column of silica and slowly eluted using hexanes as eluant. 3-(tert-butyldiphenylsilyloxymethylene)-1-cyclohexene, 33.6 g (86%), was obtained as a colorless oil which was homogenous by TLC (Rf=0.4, hexanes). The reaction mixture was washed sequentially with 150 mL portions of 1N HCl, water, brine dried over anhydrous MgSO4 The solvent was evaporated slowly eluted
Source ID: ord-1080127c897f41fa9d3ab4b7c2ec3db9Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of potassium t-butoxide (1.0M in THF, 8.27 mL, 8.27 mmol) was added dropwise to a solution of (±)-3 cyclohexene-1-methanol (853 mg, 7.60 mmol) in THF (35 mL) at 25° C. under N2. The resultant mixture was stirred at 25° C. for 30 minutes. Benzyl bromide (1.0 mL, 8.37 mmol) was added dropwise. The reaction mixture was allowed to stir at room temperature for 16 hours and then treated with saturated aqueous NH4Cl (5 mL) and concentrated. The residue was dissolved in ether (50 mL), washed with water (20 mL) and brine (20 mL), and dried over MgSO4. The solvent was evaporated under reduced pressure. The residue was subjected to radial chromatography on silica gel eluting with 5 percent EtOAc in hexane to give (±)-3-(benzyloxy)methyl-1-cyclohexene (1.42 g, 92 percent) as a colorless oil. NMR concentrated The residue was dissolved in ether (50 mL) washed with water (20 mL) and brine (20 mL) dried over MgSO4 The solvent was evaporated under reduced pressure
Source ID: ord-19959b24b2f74887b71db7146aca4fd6Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-6b82323527f043f2aebec7422d60477fConditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a mixture of 3-cyclohexene-1-methanol (Aldrich, 13.0 mL, 0.11 mol), N,N-diisopropylethylamine (43 mL, 0.244 mol) and 4-dimethylaminopyridine (2.70 g., 0.022 mol) in 375 mL of dry CH2Cl2 under N2 at 25° C. was added tert-butyldiphenylchlorosilane (32 mL, 0.123 mol). The mixture was stirred at 25° C. for 48 hours. The reaction mixture was washed sequentially with 150 mL portions of 1N HCl, water, brine and dried over anhydrous MgSO4. The solvent was evaporated. The residue was loaded onto a 4"×4" column of silica and slowly eluted using hexanes as eluant. 3-(tert-butyldiphenylsilyloxymethylene)-1-cyclohexene, 33.6 g (86%), was obtained as a colorless oil which was homogenous by TLC (Rf=0.4, hexanes). The reaction mixture was washed sequentially with 150 mL portions of 1N HCl, water, brine dried over anhydrous MgSO4 The solvent was evaporated slowly eluted
Source ID: ord-5eae52e9da1a4284bb6687483b873f0bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of potassium t-butoxide (1.0M in THF, 8.27 mL, 8.27 mmol) was added dropwise to a solution of (±)-3 cyclohexene-1-methanol (853 mg, 7.60 mmol) in THF (35 mL) at 25° C. under N2. The resultant mixture was stirred at 25° C. for 30 minutes. Benzyl bromide (1.0 mL, 8.37 mmol) was added dropwise. The reaction mixture was allowed to stir at room temperature for 16 hours and then treated with saturated aqueous NH4Cl (5 mL) and concentrated. The residue was dissolved in ether (50 mL), washed with water (20 mL) and brine (20 mL), and dried over MgSO4. The solvent was evaporated under reduced pressure. The residue was subjected to radial chromatography on silica gel eluting with 5 percent EtOAc in hexane to give (+)-3-(benzyloxy)methyl-1-cyclohexene (1.42 g, 92 percent) as a colorless oil. NMR concentrated The residue was dissolved in ether (50 mL) washed with water (20 mL) and brine (20 mL) dried over MgSO4 The solvent was evaporated under reduced pressure
Source ID: ord-d768ce33dc5b4b69a3e54aacc67be29eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of potassium t-butoxide (1.0M in THF, 8.27 mL, 8.27 mmol) was added dropwise to a solution of (±)-3 cyclohexene-1-methanol (853 mg, 7.60 mmol) in THF (35 mL) at 25° C. under N2. The resultant mixture was stirred at 25° C. for 30 minutes. Benzyl bromide (1.0 mL, 8.37 mmol) was added dropwise. The reaction mixture was allowed to stir at room temperature for 16 hours and then treated with saturated aqueous NH4Cl (5 mL) and concentrated. The residue was dissolved in ether (50 mL), washed with water (20 mL) and brine (20 mL), and dried over MgSO4. The solvent was evaporated under reduced pressure. The residue was subjected to radial chromatography on silica gel eluting with 5 percent EtOAc in hexane to give (+)-3-(benzyloxy)methyl-1-cyclohexene (1.42 g, 92 percent) as a colorless oil. NMR concentrated The residue was dissolved in ether (50 mL) washed with water (20 mL) and brine (20 mL) dried over MgSO4 The solvent was evaporated under reduced pressure
Source ID: ord-d768ce33dc5b4b69a3e54aacc67be29eConditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a mixture of 3-cyclohexene-1-methanol (Aldrich, 13.0 mL, 0.11 mol), N,N-diisopropylethylamine (43 mL, 0.244 mol) and 4-dimethylaminopyridine (2.70 g., 0.022 mol) in 375 mL of dry CH2CI2 under N2 at 25° C. was added tert-butyldiphenylchlorosilane (32 mL, 0.123 mol). The mixture was stirred at 25° C. for 48 hours. The reaction mixture was washed sequentially with 150 mL portions of 1N HCl, water, brine and dried over anhydrous MgSO4. The solvent was evaporated. The residue was loaded onto a 4"×4" column of silica and slowly eluted using hexanes as eluant. 3-(tert-butyldiphenylsilyloxymethylene)-1-cyclohexene, 33.6 g (86%), was obtained as a colorless oil which was homogenous by TLC (Rf=0.4, hexanes). The reaction mixture was washed sequentially with 150 mL portions of 1N HCl, water, brine dried over anhydrous MgSO4 The solvent was evaporated slowly eluted
Source ID: ord-d643be11dacb46f58e7f8316778b55a9Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of potassium t-butoxide (1.0M in THF, 8.27 mL, 8.27 mmol) was added dropwise to a solution of (±)-3 cyclohexene-1-methanol (853 mg, 7.60 mmol) in THF (35 mL) at 25° C. under N2. The resultant mixture was stirred at 25° C. for 30 minutes. Benzyl bromide (1.0 mL, 8.37 mmol) was added dropwise. The reaction mixture was allowed to stir at room temperature for 16 hours and then treated with saturated aqueous NH4Cl (5 mL) and concentrated. The residue was dissolved in ether (50 mL), washed with water (20 mL) and brine (20 mL), and dried over MgSO4. The solvent was evaporated under reduced pressure. The residue was subjected to radial chromatography on silica gel eluting with 5 percent EtOAc in hexane to give (±)-3-(benzyloxy)methyl-1-cyclohexene (1.42 g, 92 percent) as a colorless oil. NMR concentrated The residue was dissolved in ether (50 mL) washed with water (20 mL) and brine (20 mL) dried over MgSO4 The solvent was evaporated under reduced pressure
Source ID: ord-bd07ee38a1f64c52a1ddf849413c2068Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of potassium t-butoxide (1.0M in THF, 8.27 mL, 8.27 mmol) was added dropwise to a solution of (±)-3 cyclohexene-1-methanol (853 mg, 7.60 mmol) in THF (35 mL) at 25° C. under N2. The resultant mixture was stirred at 25° C. for 30 minutes. Benzyl bromide (1.0 mL, 8.37 mmol) was added dropwise. The reaction mixture was allowed to stir at room temperature for 16 hours and then treated with saturated aqueous NH4Cl (5 mL) and concentrated. The residue was dissolved in ether (50 mL), washed with water (20 mL) and brine (20 mL), and dried over MgSO4. The solvent was evaporated under reduced pressure. The residue was subjected to radial chromatography on silica gel eluting with 5 percent EtOAc in hexane to give (±)-3-(benzyloxy)methyl-1-cyclohexene (1.42 g, 92 percent) as a colorless oil. NMR concentrated The residue was dissolved in ether (50 mL) washed with water (20 mL) and brine (20 mL) dried over MgSO4 The solvent was evaporated under reduced pressure
Source ID: ord-bd07ee38a1f64c52a1ddf849413c2068Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a mixture of 3-cyclohexene-1-methanol (Aldrich, 13.0 mL, 0.11 mol), N,N-diisopropylethylamine (43 mL, 0.244 mol) and 4-dimethylaminopyridine (2.70 g., 0.022 mol) in 375 mL of dry CH2CI2 under B2 at 25° C. was added tert-butyldiphenylchlorosilane (32 mL, 0.123 mol). The mixture was stirred at 25° C. for 48 hours. The reaction mixture was washed sequentially with 150 mL portions of 1N HCl, water, brine and dried over anhydrous MgSO4. The solvent was evaporated. The residue was loaded onto a 4"×4" column of silica and slowly eluted using hexanes as eluant. 3-(tert-butyldiphenylsilyloxymethylene)-1-cyclohexene, 33.6 g (86%), was obtained as a colorless oil which was homogenous by TLC (Rf=0.4, hexanes). The reaction mixture was washed sequentially with 150 mL portions of 1N HCl, water, brine dried over anhydrous MgSO4 The solvent was evaporated slowly eluted
Source ID: ord-6802316d96024c16a6e97da0bc5fef93Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a mixture of 3-cyclohexene-1-methanol (Aldrich, 13.0 mL, 0.11 mol), N,N-diisopropylethylamine (43 mL, 0.244 mol) and 4-dimethylaminopyridine (2.70 g., 0.022 mol) in 375 mL of dry CH2CI2 under B2 at 25° C. was added tert-butyldiphenylchlorosilane (32 mL, 0.123 mol). The mixture was stirred at 25° C. for 48 hours. The reaction mixture was washed sequentially with 150 mL portions of 1N HCl, water, brine and dried over anhydrous MgSO4. The solvent was evaporated. The residue was loaded onto a 4"×4" column of silica and slowly eluted using hexanes as eluant. 3-(tert-butyldiphenylsilyloxymethylene)-1-cyclohexene, 33.6 g (86%), was obtained as a colorless oil which was homogenous by TLC (Rf=0.4, hexanes). The reaction mixture was washed sequentially with 150 mL portions of 1N HCl, water, brine dried over anhydrous MgSO4 The solvent was evaporated slowly eluted
Source ID: ord-6802316d96024c16a6e97da0bc5fef93PubChem References
These sources are listed in the compound's public database record.
Request a Quote
Send the required specification, quantity, destination and intended use. The CATO team will review availability and respond.