No renderable structure data available
C1=CC(=C(C=C1O)O)CCCOChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 4-(3-hydroxypropyl)benzene-1,3-diol |
|---|---|
| IUPAC Name | — |
| CAS Number | 17422-91-2 |
| Database ID | 12958403 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
4-(3-hydroxypropyl)benzene-1,3-diol (CAS 17422-91-2) 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 12958403
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-fe6e46e4d3de47ce9027cf8736a5e96bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of 4-(3-Hydroxy-propyl)-benzene-1,3-diol (3.05 g, 18.1 mmol, from Step 1) in anhydrous THF (50 mL) were added Ph3P (7.13 g, 27.2 mmol, 1.5 eq) and ADDP (6.86 g, 27.2 mmol, 1.5 eq) under argon. The mixture was stirred at rt for 17 h. The white solid was filtered off and the solvent was removed from the filtrate. 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 (1.80 g, 60.5%). 1H-NMR (CD3CN) δ 6.87 (d, 1H), 6.70 (broad, s, 1H, OH), 6.31 (dd, J=2.4, 8.2 Hz, 1H), 6.20 (d, 1H), 4.12 (t, 2H), 2.69 (t, 2H), 1.95 (m, 2H). The white solid was filtered off the solvent was removed from the filtrate The residue was purified on silica gel (flash column chromatography) eluting with 5% ethyl acetate-hexane
Source ID: ord-66eb7b3901e741bd95fa9fb2d63abc81Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of 7-hydroxycoumarin (7.0 g, 43.2 mmol) in anhydrous THF (200 mL) at rt under argon was added Lithium borohydride (2M, 65.8 mL, 129.6 mmol, 3.0 eq) solution in THF dropwise. Anhydrous methanol (1.0 mL) was added as catalyst to the reaction mixture. The mixture was heated at 65° C. for 17 h. The reaction mixture was then cooled to ambient temperature. Saturated ammonium chloride solution (40 mL) was added dropwise to the solution, followed by 1N HCl solution (40 mL). The mixture was extracted with ethyl acetate (2×100 mL). The combined organic extracts were dried (Na2SO4), filtered, and evaporated in vacuo. The residue was purified on silica gel (flash column chromatography) eluting with 30% ethyl acetate-hexane to provide the desired product as white solid (3.05 g, 42%). 1H-NMR (CD3CN) δ 6.91 (d, 1H), 6.29 (s, 1H), 6.28 (d, 1H), 3.51 (t, 2H), 2.56 (t, 2H), 1.73 (m, 2H). MS GC-MS (M+=168). The reaction mixture was then cooled to ambient temperature The mixture was extracted with ethyl acetate (2×100 mL) The combined organic extracts were dried (Na2SO4) filtered evaporated in vacuo The residue was purified on silica gel (flash column chromatography) eluting with 30% ethyl acetate-hexane
Source ID: ord-1cb196f471ee484d99d9d9b90a88f357Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of 7-hydroxycoumarin (7.0 g, 43.2 mmol) in anhydrous THF (200 mL) at rt under argon was added Lithium borohydride (2M, 65.8 mL, 129.6 mmol, 3.0 eq) solution in THF dropwise. Anhydrous methanol (1.0 mL) was added as catalyst to the reaction mixture. The mixture was heated at 65° C. for 17 h. The reaction mixture was then cooled to ambient temperature. Saturated ammonium chloride solution (40 mL) was added dropwise to the solution, followed by 1N HCl solution (40 mL). The mixture was extracted with ethyl acetate (2×100 mL). The combined organic extracts were dried (Na2SO4), filtered, and evaporated in vacuo. The residue was purified on silica gel (flash column chromatography) eluting with 30% ethyl acetate-hexane to provide the desired product as white solid (3.05 g, 42%). 1H-NMR (CD3CN) δ 6.91 (d, 1H), 6.29 (s, 1H), 6.28 (d, 1H), 3.51 (t, 2H), 2.56 (t, 2H), 1.73 (m, 2H). MS GC-MS (M+=168). The reaction mixture was then cooled to ambient temperature The mixture was extracted with ethyl acetate (2×100 mL) The combined organic extracts were dried (Na2SO4) filtered evaporated in vacuo The residue was purified on silica gel (flash column chromatography) eluting with 30% ethyl acetate-hexane
Source ID: ord-1cb196f471ee484d99d9d9b90a88f357Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of 4-(3-Hydroxy-propyl)-benzene-1,3-diol (3.05 g, 18.1 mmol, from Step 1) in anhydrous THF (50 mL ) were added Ph3P (7.13 g, 27.2 mmol, 1.5 eq) and ADDP (6.86 g, 27.2 mmol, 1.5 eq ) under argon. The mixture was stirred at rt for 17 h. The white solid was filtered off and the solvent was removed from the filtrate. 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 (1.80 g, 60.5%). 1H-NMR (CD3CN) δ 6.87 (d, 1H), 6.70 (broad, s, 1H, OH), 6.31 (dd, J=2.4, 8.2 Hz, 1H), 6.20 (d, 1H), 4.12 (t, 2H), 2.69 (t, 2H), 1.95 (m, 2H). The white solid was filtered off the solvent was removed from the filtrate The residue was purified on silica gel (flash column chromatography) eluting with 5% ethyl acetate-hexane
Source ID: ord-e754183c2b0548268128ce771017074eConditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of 7-hydroxycoumarin (7.0 g, 43.2 mmol ) in anhydrous THF (200 mL ) at rt under argon was added Lithium borohydride (2M, 65.8 mL, 129.6 mmol, 3.0 eq) solution in THF dropwise. Anhydrous methanol (1.0 mL) was added as catalyst to the reaction mixture. The mixture was heated at 65° C. for 17 h. The reaction mixture was then cooled to ambient temperature. Saturated ammonium chloride solution (40 mL) was added dropwise to the solution, followed by 1N HCl solution (40 mL). The mixture was extracted with ethyl acetate (2×100 mL). The combined organic extracts were dried (Na2SO4), filtered, and evaporated in vacuo. The residue was purified on silica gel (flash column chromatography) eluting with 30% ethyl acetate-hexane to provide the desired product as white solid (3.05 g, 42%). 1H-NMR (CD3CN) δ 6.91 (d, 1H), 6.29 (s, 1H), 6.28 (d, 1H), 3.51 (t, 2H), 2.56 (t, 2H), 1.73 (m, 2H). MS GC-MS (M+=168). The reaction mixture was then cooled to ambient temperature The mixture was extracted with ethyl acetate (2×100 mL) The combined organic extracts were dried (Na2SO4) filtered evaporated in vacuo The residue was purified on silica gel (flash column chromatography) eluting with 30% ethyl acetate-hexane
Source ID: ord-2fc1d2009a2d44c289d36fbe7124f4dfConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of 4-(3-Hydroxy-propyl)-benzene-1,3-diol (3.05 g, 18.1 mmol, from Step 1) in anhydrous THF (50 mL ) were added Ph3P (7.13 g, 27.2 mmol, 1.5 eq) and ADDP (6.86 g, 27.2 mmol, 1.5 eq ) under argon. The mixture was stirred at rt for 17 h. The white solid was filtered off and the solvent was removed from the filtrate. 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 (1.80 g, 60.5%). 1H-NMR (CD3CN) δ 6.87 (d, 1H), 6.70 (broad, s, 1H, OH), 6.31 (dd, J=2.4, 8.2 Hz, 1H), 6.20 (d, 1H), 4.12 (t, 2H), 2.69 (t, 2H), 1.95 (m, 2H). The white solid was filtered off the solvent was removed from the filtrate The residue was purified on silica gel (flash column chromatography) eluting with 5% ethyl acetate-hexane
Source ID: ord-e754183c2b0548268128ce771017074eConditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of 7-hydroxycoumarin (7.0 g, 43.2 mmol ) in anhydrous THF (200 mL ) at rt under argon was added Lithium borohydride (2M, 65.8 mL, 129.6 mmol, 3.0 eq) solution in THF dropwise. Anhydrous methanol (1.0 mL) was added as catalyst to the reaction mixture. The mixture was heated at 65° C. for 17 h. The reaction mixture was then cooled to ambient temperature. Saturated ammonium chloride solution (40 mL) was added dropwise to the solution, followed by 1N HCl solution (40 mL). The mixture was extracted with ethyl acetate (2×100 mL). The combined organic extracts were dried (Na2SO4), filtered, and evaporated in vacuo. The residue was purified on silica gel (flash column chromatography) eluting with 30% ethyl acetate-hexane to provide the desired product as white solid (3.05 g, 42%). 1H-NMR (CD3CN) δ 6.91 (d, 1H), 6.29 (s, 1H), 6.28 (d, 1H), 3.51 (t, 2H), 2.56 (t, 2H), 1.73 (m, 2H). MS GC-MS (M+=168). The reaction mixture was then cooled to ambient temperature The mixture was extracted with ethyl acetate (2×100 mL) The combined organic extracts were dried (Na2SO4) filtered evaporated in vacuo The residue was purified on silica gel (flash column chromatography) eluting with 30% ethyl acetate-hexane
Source ID: ord-2fc1d2009a2d44c289d36fbe7124f4dfConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-fe6e46e4d3de47ce9027cf8736a5e96bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of 4-(3-Hydroxy-propyl)-benzene-1,3-diol (3.05 g, 18.1 mmol, from Step 1) in anhydrous THF (50 mL) were added Ph3P (7.13 g, 27.2 mmol, 1.5 eq) and ADDP (6.86 g, 27.2 mmol, 1.5 eq) under argon. The mixture was stirred at rt for 17 h. The white solid was filtered off and the solvent was removed from the filtrate. 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 (1.80 g, 60.5%). 1H-NMR (CD3CN) δ 6.87 (d, 1H), 6.70 (broad, s, 1H, OH), 6.31 (dd, J=2.4, 8.2 Hz, 1H), 6.20 (d, 1H), 4.12 (t, 2H), 2.69 (t, 2H), 1.95 (m, 2H). The white solid was filtered off the solvent was removed from the filtrate The residue was purified on silica gel (flash column chromatography) eluting with 5% ethyl acetate-hexane
Source ID: ord-66eb7b3901e741bd95fa9fb2d63abc81Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of 7-hydroxycoumarin (7.0 g, 43.2 mmol) in anhydrous THF (200 mL) at rt under argon was added Lithium borohydride (2M, 65.8 mL, 129.6 mmol, 3.0 eq) solution in THF dropwise. Anhydrous methanol (1.0 mL) was added as catalyst to the reaction mixture. The mixture was heated at 65° C. for 17 h. The reaction mixture was then cooled to ambient temperature. Saturated ammonium chloride solution (40 mL) was added dropwise to the solution, followed by 1N HCl solution (40 mL). The mixture was extracted with ethyl acetate (2×100 mL). The combined organic extracts were dried (Na2SO4), filtered, and evaporated in vacuo. The residue was purified on silica gel (flash column chromatography) eluting with 30% ethyl acetate-hexane to provide the desired product as white solid (3.05 g, 42%). 1H-NMR (CD3CN) δ 6.91 (d, 1H), 6.29 (s, 1H), 6.28 (d, 1H), 3.51 (t, 2H), 2.56 (t, 2H), 1.73 (m, 2H). MS GC-MS (M+=168). The reaction mixture was then cooled to ambient temperature The mixture was extracted with ethyl acetate (2×100 mL) The combined organic extracts were dried (Na2SO4) filtered evaporated in vacuo The residue was purified on silica gel (flash column chromatography) eluting with 30% ethyl acetate-hexane
Source ID: ord-1cb196f471ee484d99d9d9b90a88f357Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of 4-(3-Hydroxy-propyl)-benzene-1,3-diol (3.05 g, 18.1 mmol, from Step 1) in anhydrous THF (50 mL ) were added Ph3P (7.13 g, 27.2 mmol, 1.5 eq) and ADDP (6.86 g, 27.2 mmol, 1.5 eq ) under argon. The mixture was stirred at rt for 17 h. The white solid was filtered off and the solvent was removed from the filtrate. 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 (1.80 g, 60.5%). 1H-NMR (CD3CN) δ 6.87 (d, 1H), 6.70 (broad, s, 1H, OH), 6.31 (dd, J=2.4, 8.2 Hz, 1H), 6.20 (d, 1H), 4.12 (t, 2H), 2.69 (t, 2H), 1.95 (m, 2H). The white solid was filtered off the solvent was removed from the filtrate The residue was purified on silica gel (flash column chromatography) eluting with 5% ethyl acetate-hexane
Source ID: ord-e754183c2b0548268128ce771017074ePubChem References
These sources are listed in the compound's public database record.
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