No renderable structure data available
CC1(CCC2=C(O1)C=C(C=C2)O)CChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 2,2-dimethyl-3,4-dihydrochromen-7-ol |
|---|---|
| IUPAC Name | — |
| CAS Number | 31005-72-8 |
| Database ID | 11041281 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
2,2-dimethyl-3,4-dihydrochromen-7-ol (CAS 31005-72-8) 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 11041281
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-a6968b978a654587844a67057c23a884Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-e313b21c550e4637a1c5faf70eb2ebccConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-a6968b978a654587844a67057c23a884Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-a6968b978a654587844a67057c23a884Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: In a 250 mL round-bottom flask was placed 2,2-dimethyl-Chroman-7-ol (1.76 g, 9.87 mmol, from Step 4-1-2) in 30 mL of dry dichloroethane under argon. The solution was cooled to 0° C. where boron trichloride (10.8 mL, 1M in CH2Cl2, 10.8 mmol, 1.1 eq) was added dropwise. At this point, methyl thiocyanate (0.80 g, 10.8 mmol, 1.1 eq) was added followed by aluminum trichloride (1.32 g, 9.87 mmol, 1 eq). The reaction was allowed to warm up to rt and stirred for 17 h. The reaction mixture was cooled down to 0° C. and 10 mL of 50% w/w NaOH was added to adjust the solution to PH—14, followed by 40 mL of water. The solution was then refluxed at 65° C. for 2 h. The solution was allowed to cool to ambient temperature. The aqueous layer was washed with dichloromethane (20 mL). The aqueous solution was transferred to an Erlenmeyer flask and acidified to pH˜1 with conc. HCl. This solution was then extracted with EtOAc (3×20 mL) and the combined organic layers were dried over Na2SO4, filtered and evaporated. The residue was purified on silica gel (flash column chromatography) eluting with 5% ethyl acetate-hexane followed by 20% ethyl acetate-hexane to provide the desired product as white solid. The desired product was white solid (0.33 g, 16.5%). 1H-NMR (CD3CN) δ 7.93 (broad s, 1H, OH), 7.26 (s, 1H), 6.28 (s, 1H), 2.69 (t, 2H), 1.80 (t, 2H), 1.32 (s, 6H). In a 250 mL round-bottom flask was placed was added dropwise The reaction mixture was cooled down to 0° C. The solution was then refluxed at 65° C. for 2 h to cool to ambient temperature The aqueous layer was washed with dichloromethane (20 mL) This solution was then extracted with EtOAc (3×20 mL) the combined organic layers were dried over Na2SO4 filtered evaporated The residue was purified on silica gel (flash column chromatography) eluting with 5% ethyl acetate-hexane
Source ID: ord-0bc4ce0359cc4fe5a5c6139ee262a01aConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of 7-Methoxy-2,2-dimethyl-chroman (4.55 g, 23.7 mmol, from step 1) in anhydrous dichloromethane (50 mL) was added 1M BBr3 (72.86 mL, 47.4 mmol, 2.0 eq) via cannula over 10 min. The resulting dark brown solution was stirred at rt for 17 h. Saturated solution of NaHCO3 (50 mL) was added and extracted with CH2Cl2 (3×50 mL. The combined organic layers were dried over Na2SO4, filtered and evaporated. The residue was purified on silica gel (flash column chromatography) eluting with 5% ethyl acetate-hexane followed by 20% ethyl acetate-hexane to provide the desired product as white solid (1.76 g, 42%). 1H-NMR (CD3CN) δ 6.89 (d, J=8.5 Hz, 1H), 6.68 (broad, s, 1H, OH), 6.31 (dd, J=2.4, 8.5 Hz, 1H), 6.15 (d, J=2.4 Hz, 1H), 2.69 (t, 2H), 1.79 (t, 2H), 1.31 (s, 6H). MS LC-MS (MH+=179). extracted with CH2Cl2 (3×50 mL The combined organic layers were dried over Na2SO4 filtered evaporated The residue was purified on silica gel (flash column chromatography) eluting with 5% ethyl acetate-hexane
Source ID: ord-22d881df84794970a63c9898587c5e27Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of 7-Methoxy-2,2-dimethyl-chroman (4.55 g, 23.7 mmol, from step 1) in anhydrous dichloromethane (50 mL) was added 1M BBr3 (72.86 mL, 47.4 mmol, 2.0 eq) via cannula over 10 min. The resulting dark brown solution was stirred at rt for 17 h. Saturated solution of NaHCO3 (50 mL) was added and extracted with CH2Cl2 (3×50 mL. The combined organic layers were dried over Na2SO4, filtered and evaporated. The residue was purified on silica gel (flash column chromatography) eluting with 5% ethyl acetate-hexane followed by 20% ethyl acetate-hexane to provide the desired product as white solid (1.76 g, 42%). 1H-NMR (CD3CN) δ 6.89 (d, J=8.5 Hz, 1H), 6.68 (broad, s, 1H, OH), 6.31 (dd, J=2.4, 8.5 Hz, 1H), 6.15 (d, J=2.4 Hz, 1H), 2.69 (t, 2H), 1.79 (t, 2H), 1.31 (s, 6H). MS LC-MS (MH+=179). extracted with CH2Cl2 (3×50 mL The combined organic layers were dried over Na2SO4 filtered evaporated The residue was purified on silica gel (flash column chromatography) eluting with 5% ethyl acetate-hexane
Source ID: ord-22d881df84794970a63c9898587c5e27Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: In a 250 mL round-bottom flask was placed 2,2-dimethyl-Chroman-7-ol (1.76 g, 9.87 mmol, from Step 4-1-2) in 30 mL of dry dichloroethane under argon. The solution was cooled to 0° C. where boron trichloride (10.8 mL, 1M in CH2Cl2, 10.8 mmol, 1.1 eq) was added dropwise. At this point, methyl thiocyanate (0.80 g, 10.8 mmol, 1.1 eq) was added followed by aluminum trichloride (1.32 g, 9.87 mmol, 1 eq). The reaction was allowed to warm up to rt and stirred for 17 h. The reaction mixture was cooled down to 0° C. and 10 mL of 50% w/w NaOH was added to adjust the solution to PH˜14, followed by 40 mL of water. The solution was then refluxed at 65° C. for 2 h. The solution was allowed to cool to ambient temperature. The aqueous layer was washed with dichloromethane (20 mL). The aqueous solution was transferred to an Erlenmeyer flask and acidified to pH˜1 with conc. HCl. This solution was then extracted with EtOAc (3×20 mL) and the combined organic layers were dried over Na2SO4, filtered and evaporated. The residue was purified on silica gel (flash column chromatography) eluting with 5% ethyl acetate-hexane followed by 20% ethyl acetate-hexane to provide the desired product as white solid. The desired product was white solid (0.33 g, 16.5% ). 1H-NMR (CD3CN) δ 7.93 (broad s, 1H, OH), 7.26 (s, 1H), 6.28 (s, 1H), 2.69 (t, 2H), 1.80 (t, 2H), 1.32 (s, 6H). In a 250 mL round-bottom flask was placed was added dropwise The reaction mixture was cooled down to 0° C. The solution was then refluxed at 65° C. for 2 h to cool to ambient temperature The aqueous layer was washed with dichloromethane (20 mL) This solution was then extracted with EtOAc (3×20 mL) the combined organic layers were dried over Na2SO4 filtered evaporated The residue was purified on silica gel (flash column chromatography) eluting with 5% ethyl acetate-hexane
Source ID: ord-c2b90f4bef874b4c92fa77c27e2fc91aConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of 7-Methoxy-2,2-dimethyl-chroman (4.55 g, 23.7 mmol, from step 1) in anhydrous dichloromethane (50 mL) was added 1M BBr3 (72.86 mL, 47.4 mmol, 2.0 eq ) via cannula over 10 min. The resulting dark brown solution was stirred at rt for 17 h. Saturated solution of NaHCO3 (50 mL) was added and extracted with CH2Cl2 (3×50 mL. The combined organic layers were dried over Na2SO4, filtered and evaporated. The residue was purified on silica gel (flash column chromatography) eluting with 5% ethyl acetate-hexane followed by 20% ethyl acetate-hexane to provide the desired product as white solid (1.76 g, 42%). 1H-NMR (CD3CN) δ 6.89 (d, J=8.5 Hz, 1H), 6.68 (broad, s, 1H, OH), 6.31 (dd, J=2.4, 8.5 Hz, 1H), 6.15 (d, J=2.4Hz, 1H ), 2.69 (t, 2H ), 1.79 (t, 2H), 1.31 (s, 6H). MS LC-MS (MH+=179). extracted with CH2Cl2 (3×50 mL The combined organic layers were dried over Na2SO4 filtered evaporated The residue was purified on silica gel (flash column chromatography) eluting with 5% ethyl acetate-hexane
Source ID: ord-ca1bbde6e1a848948f3665919bc6fdbbConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-e313b21c550e4637a1c5faf70eb2ebccConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: In a 250 mL round-bottom flask was placed 2,2-dimethyl-Chroman-7-ol (1.76 g, 9.87 mmol, from Step 4-1-2) in 30 mL of dry dichloroethane under argon. The solution was cooled to 0° C. where boron trichloride (10.8 mL, 1M in CH2Cl2, 10.8 mmol, 1.1 eq) was added dropwise. At this point, methyl thiocyanate (0.80 g, 10.8 mmol, 1.1 eq) was added followed by aluminum trichloride (1.32 g, 9.87 mmol, 1 eq). The reaction was allowed to warm up to rt and stirred for 17 h. The reaction mixture was cooled down to 0° C. and 10 mL of 50% w/w NaOH was added to adjust the solution to PH˜14, followed by 40 mL of water. The solution was then refluxed at 65° C. for 2 h. The solution was allowed to cool to ambient temperature. The aqueous layer was washed with dichloromethane (20 mL). The aqueous solution was transferred to an Erlenmeyer flask and acidified to pH˜1 with conc. HCl. This solution was then extracted with EtOAc (3×20 mL) and the combined organic layers were dried over Na2SO4, filtered and evaporated. The residue was purified on silica gel (flash column chromatography) eluting with 5% ethyl acetate-hexane followed by 20% ethyl acetate-hexane to provide the desired product as white solid. The desired product was white solid (0.33 g, 16.5% ). 1H-NMR (CD3CN) δ 7.93 (broad s, 1H, OH), 7.26 (s, 1H), 6.28 (s, 1H), 2.69 (t, 2H), 1.80 (t, 2H), 1.32 (s, 6H). In a 250 mL round-bottom flask was placed was added dropwise The reaction mixture was cooled down to 0° C. The solution was then refluxed at 65° C. for 2 h to cool to ambient temperature The aqueous layer was washed with dichloromethane (20 mL) This solution was then extracted with EtOAc (3×20 mL) the combined organic layers were dried over Na2SO4 filtered evaporated The residue was purified on silica gel (flash column chromatography) eluting with 5% ethyl acetate-hexane
Source ID: ord-c2b90f4bef874b4c92fa77c27e2fc91aConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of 7-Methoxy-2,2-dimethyl-chroman (4.55 g, 23.7 mmol, from step 1) in anhydrous dichloromethane (50 mL) was added 1M BBr3 (72.86 mL, 47.4 mmol, 2.0 eq ) via cannula over 10 min. The resulting dark brown solution was stirred at rt for 17 h. Saturated solution of NaHCO3 (50 mL) was added and extracted with CH2Cl2 (3×50 mL. The combined organic layers were dried over Na2SO4, filtered and evaporated. The residue was purified on silica gel (flash column chromatography) eluting with 5% ethyl acetate-hexane followed by 20% ethyl acetate-hexane to provide the desired product as white solid (1.76 g, 42%). 1H-NMR (CD3CN) δ 6.89 (d, J=8.5 Hz, 1H), 6.68 (broad, s, 1H, OH), 6.31 (dd, J=2.4, 8.5 Hz, 1H), 6.15 (d, J=2.4Hz, 1H ), 2.69 (t, 2H ), 1.79 (t, 2H), 1.31 (s, 6H). MS LC-MS (MH+=179). extracted with CH2Cl2 (3×50 mL The combined organic layers were dried over Na2SO4 filtered evaporated The residue was purified on silica gel (flash column chromatography) eluting with 5% ethyl acetate-hexane
Source ID: ord-ca1bbde6e1a848948f3665919bc6fdbbPubChem References
These sources are listed in the compound's public database record.
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