No renderable structure data available
CC1=CC2=C(O1)C=C(C=C2)OChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 2-methyl-1-benzofuran-6-ol |
|---|---|
| IUPAC Name | — |
| CAS Number | 54584-24-6 |
| Database ID | 12203498 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
2-methyl-1-benzofuran-6-ol (CAS 54584-24-6) 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 12203498
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-f0fba0046d164a03877cc0dd0d315771Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: This material was prepared from 6-hydroxy-2-methylbenzofuran (654 mg, 4.41 mmole) by treatment with acetyl chloride (0.41 ml, 5.74 mmole) and triethylamine (0.74 ml, 5.30 mmole) in a manner as previously described for 8b to give the desired product as an oil (850 mg, ˜quant). 1H NMR (CDCl3) δ7.41 (1H, d, J=8.3 Hz), 7.13 (1H, s), 6.88 (1H, dd, J=8.3, 1.9 Hz), 6.32 (1H, s), 2.42 (3H, s), 2.30 (3H, s).
Source ID: ord-7159ae4a94ae4c2280514043293c1efaConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: This material was prepared from 6-methoxy-2-methylbenzofuran (1.00 g, 6.17 mmole) by treatment with BBr3 in a manner as previously described for 1d to give a colorless oil (690 mg, 75%) which solidified on standing. 1H NMR (DMSO-d6) δ9.32 (1H, s), 7.23 (1H, d, J=8.3 Hz), 6.80 (1H, s), 6.64 (1H, d, J=8.3 Hz), 6.37 (1H, s), 2.35 (3H, s).
Source ID: ord-2b3273bbd7e34993a54335a599cf626eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: This material was prepared from 6-methoxy-2-methylbenzofuran (1.00 g, 6.17 mmole) by treatment with BBr3 in a manner as previously described for 1d to give a colorless oil (690 mg, 75%) which solidified on standing. 1H NMR (DMSO-d6) δ9.32 (1H, s), 7.23 (1H, d, J=8.3 Hz), 6.80 (1H, s), 6.64 (1H, d, J=8.3 Hz), 6.37 (1H, s), 2.35 (3H, s).
Source ID: ord-2b3273bbd7e34993a54335a599cf626eConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of 6-Methoxy-2-methyl-benzofuran 125-A (1.76 g, 10.85mmol) in 45 ml of CH2Cl2 at −5° C. was added BBr3 (24 ml of 1M BBr3 in CH2Cl2, 16 28 mmol). The reaction was allowed to warm to 0° C. and stirred at that temperature for 1.5 hr. The reaction was poured into a mixture of ice and saturated aqueous NaHCO3 and layers were separated. The aqueous layer was re-extracted with CH2Cl2. The combined organic layers were dried (MgSO4) and concentrated under reduced pressure to a brown oil. The residue was chromatographed on silica gel eluting CH2Cl2 to give 872 mg (54%) of 6-Hydroxy-2-methyl-benzofuran 125-B. were separated The aqueous layer was re-extracted with CH2Cl2 The combined organic layers were dried (MgSO4) concentrated under reduced pressure to a brown oil The residue was chromatographed on silica gel eluting CH2Cl2
Source ID: ord-c56fc70fc36d46b1b8a26688069fc83bConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of 6-Methoxy-2-methyl-benzofuran 125-A (1.76 g, 10.85mmol) in 45 ml of CH2Cl2 at −5° C. was added BBr3 (24 ml of 1M BBr3 in CH2Cl2, 16 28 mmol). The reaction was allowed to warm to 0° C. and stirred at that temperature for 1.5 hr. The reaction was poured into a mixture of ice and saturated aqueous NaHCO3 and layers were separated. The aqueous layer was re-extracted with CH2Cl2. The combined organic layers were dried (MgSO4) and concentrated under reduced pressure to a brown oil. The residue was chromatographed on silica gel eluting CH2Cl2 to give 872 mg (54%) of 6-Hydroxy-2-methyl-benzofuran 125-B. were separated The aqueous layer was re-extracted with CH2Cl2 The combined organic layers were dried (MgSO4) concentrated under reduced pressure to a brown oil The residue was chromatographed on silica gel eluting CH2Cl2
Source ID: ord-c56fc70fc36d46b1b8a26688069fc83bConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-f0fba0046d164a03877cc0dd0d315771Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of 6-Methoxy-2-methyl-benzofuran 125-A (1.76 g, 10.85 mmol) in 45 ml of CH2Cl2 at −5° C. was added BBr3 (24 ml of 1M BBr3 in CH2Cl2, 16.28 mmol). The reaction was allowed to warm to 0° C. and stirred at that temperature for 1.5 hr. The reaction was poured into a mixture of ice and saturated aqueous NaHCO3 and layers were separated. The aqueous layer was re-extracted with CH2Cl2. The combined organic layers were dried (MgSO4) and concentrated under reduced pressure to a brown oil. The residue was chromatographed on silica gel eluting CH2Cl2 to give 872 mg (54%) of 6-Hydroxy-2-methyl-benzofuran 125-B. Anal calc'd for C9H8O2: C, 72.96; H, 5.44. Found: C, 72.72; H, 5.43. were separated The aqueous layer was re-extracted with CH2Cl2 The combined organic layers were dried (MgSO4) concentrated under reduced pressure to a brown oil The residue was chromatographed on silica gel eluting CH2Cl2
Source ID: ord-aa59aed52a5f437995ff6196feb0dc36Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: This material was prepared from 6-hydroxy-2-methylbenzofuran (654 mg, 4.41 mmole) by treatment with acetyl chloride (0.41 ml, 5.74 mmole) and triethylamine (0.74 ml, 5.30 mmole) in a manner as previously described for 8b to give the desired product as an oil (850 mg, ˜quant). 1H NMR (CDCl3) δ 7.41 (1H, d, J=8.3 Hz), 7.13 (1H, s), 6.88 (1H, dd, J=8.3, 1.9 Hz), 6.32 (1H, s), 2.42 (3H, s), 2.30 (3H, s).
Source ID: ord-7f31596760d84cc6954b7dfd9dccfbc0Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: This material was prepared from 6-methoxy-2-methylbenzofuran (1.00 g, 6.17 mmole) by treatment with BBr3 in a manner as previously described for 1d to give a colorless oil (690 mg, 75%) which solidified on standing. 1H NMR (DMSO-d6) δ 9.32 (1H, s), 7.23 (1H, d, J=8.3 Hz), 6.80 (1H, s),6.64 (1H, d, J=8.3 Hz), 6.37 (1H, s), 2.35 (3H, s).
Source ID: ord-6ed2fc5e5ac64b388d439433541d20c8Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: This material was prepared from 6-hydroxy-2-methylbenzofuran (654 mg, 4.41 mmole) by treatment with acetyl chloride (0.41 ml, 5.74 mmole) and triethylamine (0.74 ml, 5.30 mmole) in a manner as previously described for 8b to give the desired product as an oil (850 mg, ˜quant). 1H NMR (CDCl3) δ7.41 (1H, d, J=8.3 Hz), 7.13 (1H, s), 6.88 (1H, dd, J=8.3, 1.9 Hz), 6.32 (1H, s), 2.42 (3H, s), 2.30 (3H, s).
Source ID: ord-7159ae4a94ae4c2280514043293c1efaConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: This material was prepared from 6-methoxy-2-methylbenzofuran (1.00 g, 6.17 mmole) by treatment with BBr3 in a manner as previously described for 1d to give a colorless oil (690 mg, 75%) which solidified on standing. 1H NMR (DMSO-d6) δ9.32 (1H, s), 7.23 (1H, d, J=8.3 Hz), 6.80 (1H, s), 6.64 (1H, d, J=8.3 Hz), 6.37 (1H, s), 2.35 (3H, s).
Source ID: ord-2b3273bbd7e34993a54335a599cf626ePubChem References
These sources are listed in the compound's public database record.
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