No renderable structure data available
CC1=C(C=CC=C1O)C#NChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 3-hydroxy-2-methylbenzonitrile |
|---|---|
| IUPAC Name | — |
| CAS Number | 55289-04-8 |
| Database ID | 22616094 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
3-hydroxy-2-methylbenzonitrile (CAS 55289-04-8) 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 22616094
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-3cb0f1a5e6a140a48559ae19f31160f3Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-3cb0f1a5e6a140a48559ae19f31160f3Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 3-methoxy-2-methylbenzonitrile [(1 g, 6.79 mmol) U.S. Pat. No. 5,965,766, p 6] and tetra nbutyl ammonium iodide (4.12 g, 17 mmol) in dichloromethane (15 mL) was cooled to −78° C. and purged with nitrogen. Boron trichloride (1M in dichloromethane, 17 mL, 17 mmol) was added dropwise and the mixture was stirred for 15 minutes at −78° C. and at room temperature for 3 hours. The reaction mixture was quenched with water, stirred for 30 minutes and concentrated in vacuo. The aqueous residue was extracted with diethyl ether and the organic solution was washed with water (×5), dried over magnesium sulfate and concentrated in vacuo to afford the title compound as a brown solid in 91% yield, 826 mg. 1H NMR (400 MHz, CDCl3) δ: 2.20 (s, 3H), 7.10 (m, 1H), 7.20 (d, 1H), 10.10 (s, 1H); LRMS APCI m/z 132 [M−H]− purged with nitrogen The reaction mixture was quenched with water stirred for 30 minutes concentrated in vacuo The aqueous residue was extracted with diethyl ether the organic solution was washed with water (×5) dried over magnesium sulfate concentrated in vacuo
Source ID: ord-d99f0e66523d45b69f0a10aec9fce739Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 3-methoxy-2-methylbenzonitrile [(1 g, 6.79 mmol) U.S. Pat. No. 5,965,766, p 6] and tetra nbutyl ammonium iodide (4.12 g, 17 mmol) in dichloromethane (15 mL) was cooled to −78° C. and purged with nitrogen. Boron trichloride (1M in dichloromethane, 17 mL, 17 mmol) was added dropwise and the mixture was stirred for 15 minutes at −78° C. and at room temperature for 3 hours. The reaction mixture was quenched with water, stirred for 30 minutes and concentrated in vacuo. The aqueous residue was extracted with diethyl ether and the organic solution was washed with water (×5), dried over magnesium sulfate and concentrated in vacuo to afford the title compound as a brown solid in 91% yield, 826 mg. 1H NMR (400 MHz, CDCl3) δ: 2.20 (s, 3H), 7.10 (m, 1H), 7.20 (d, 1H), 10.10 (s, 1H); LRMS APCI m/z 132 [M−H]− purged with nitrogen The reaction mixture was quenched with water stirred for 30 minutes concentrated in vacuo The aqueous residue was extracted with diethyl ether the organic solution was washed with water (×5) dried over magnesium sulfate concentrated in vacuo
Source ID: ord-d99f0e66523d45b69f0a10aec9fce739Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 3-hydroxy-2-methylbenzonitrile (7.00 g) in THF (100 mL) were added triethylamine (13.1 g), magnesium chloride (12.4 g) and paraformaldehyde (6.60 g), and the mixture was heated with reflux for 16 hr under nitrogen atmosphere. The reaction mixture was poured into 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by flash silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (1.30 g). the mixture was heated with reflux for 16 hr under nitrogen atmosphere the mixture was extracted with ethyl acetate The organic layer was dried over anhydrous sodium sulfate the solvent was evaporated under reduced pressure The residue was purified by flash silica gel column chromatography (ethyl acetate/petroleum ether)
Source ID: ord-0eca85aa837d46939ac19b533649bf5cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 3-hydroxy-2-methylbenzonitrile (7.00 g) in THF (100 mL) were added triethylamine (13.1 g), magnesium chloride (12.4 g) and paraformaldehyde (6.60 g), and the mixture was heated with reflux for 16 hr under nitrogen atmosphere. The reaction mixture was poured into 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by flash silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (1.30 g). the mixture was heated with reflux for 16 hr under nitrogen atmosphere the mixture was extracted with ethyl acetate The organic layer was dried over anhydrous sodium sulfate the solvent was evaporated under reduced pressure The residue was purified by flash silica gel column chromatography (ethyl acetate/petroleum ether)
Source ID: ord-0eca85aa837d46939ac19b533649bf5cConditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 3-bromo-2-methylphenol (20.0 g) in DMF (250 mL) were added copper(I) cyanide (19.0 g) and tetrakis(triphenylphosphine)palladium(0) (3.70 g), and the mixture was heated with stirring at 120° C. for 16 hr under nitrogen atmosphere. The reaction mixture was poured into water, and the mixture was filtered. The filtrate was extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was washed with tert-butyl methyl ether to give the title compound (7.00 g). the mixture was heated the mixture was filtered The filtrate was extracted with ethyl acetate the organic layer was dried over anhydrous sodium sulfate The solvent was evaporated under reduced pressure the residue was washed with tert-butyl methyl ether
Source ID: ord-ad803e8f7a134729a6582064b93c2c91Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 3-methoxy-2-methylbenzonitrile [(1 g, 6.79 mmol) U.S. Pat. No. 5,965,766, p6] and tetra nbutyl ammonium iodide (4.12 g, 17 mmol) in dichloromethane (15 mL) was cooled to −78° C. and purged with nitrogen. Boron trichloride (1M in dichloromethane, 17 mL, 17 mmol) was added dropwise and the mixture was stirred for 15 minutes at −78° C. and at room temperature for 3 hours. The reaction mixture was quenched with water, stirred for 30 minutes and concentrated in vacuo. The aqueous residue was extracted with diethyl ether and the organic solution was washed with water (×5), dried over magnesium sulfate and concentrated in vacuo to afford the title compound as a brown solid in 91% yield, 826 mg. 1H NMR (400 MHz, CDCl3) δ: 2.20 (s, 3H), 7.10 (m, 1H), 7.20 (d, 1H), 10.10 (s, 1H); LRMS APCI m/z 132 [M−H]− purged with nitrogen The reaction mixture was quenched with water stirred for 30 minutes concentrated in vacuo The aqueous residue was extracted with diethyl ether the organic solution was washed with water (×5) dried over magnesium sulfate concentrated in vacuo
Source ID: ord-a91de27ee48c4ea5a47bb4f07022a2fdConditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 3-methoxy-2-methylbenzonitrile [(1 g, 6.79 mmol) U.S. Pat. No. 5,965,766, p6] and tetra nbutyl ammonium iodide (4.12 g, 17 mmol) in dichloromethane (15 mL) was cooled to −78° C. and purged with nitrogen. Boron trichloride (1M in dichloromethane, 17 mL, 17 mmol) was added dropwise and the mixture was stirred for 15 minutes at −78° C. and at room temperature for 3 hours. The reaction mixture was quenched with water, stirred for 30 minutes and concentrated in vacuo. The aqueous residue was extracted with diethyl ether and the organic solution was washed with water (×5), dried over magnesium sulfate and concentrated in vacuo to afford the title compound as a brown solid in 91% yield, 826 mg. 1H NMR (400 MHz, CDCl3) δ: 2.20 (s, 3H), 7.10 (m, 1H), 7.20 (d, 1H), 10.10 (s, 1H); LRMS APCI m/z 132 [M−H]− purged with nitrogen The reaction mixture was quenched with water stirred for 30 minutes concentrated in vacuo The aqueous residue was extracted with diethyl ether the organic solution was washed with water (×5) dried over magnesium sulfate concentrated in vacuo
Source ID: ord-a91de27ee48c4ea5a47bb4f07022a2fdConditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 3-methoxy-2-methylbenzonitrile [(1 g, 6.79 mmol) U.S. Pat. No. 5,965,766, p6] and tetra nbutyl ammonium iodide (4.12 g, 17 mmol) in dichloromethane (15 mL) was cooled to −78° C. and purged with nitrogen. Boron trichloride (1M in dichloromethane, 17 mL, 17 mmol) was added dropwise and the mixture was stirred for 15 minutes at −78° C. and at room temperature for 3 hours. The reaction mixture was quenched with water, stirred for 30 minutes and concentrated in vacuo. The aqueous residue was extracted with diethyl ether and the organic solution was washed with water (×5), dried over magnesium sulfate and concentrated in vacuo to afford the title compound as a brown solid in 91% yield, 826 mg. 1H NMR(400 MHz, CDCl3) δ: 2.20 (s, 3H), 7.10 (m, 1H), 7.20 (d, 1H), 10.10 (s, 1H); LRMS APCI m/z 132 [M−H]− purged with nitrogen The reaction mixture was quenched with water stirred for 30 minutes concentrated in vacuo The aqueous residue was extracted with diethyl ether the organic solution was washed with water (×5) dried over magnesium sulfate concentrated in vacuo
Source ID: ord-d321f6df14164a3a96d519f2d919818bConditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 3-methoxy-2-methylbenzonitrile [(1 g, 6.79 mmol) U.S. Pat. No. 5,965,766, p 6] and tetra nbutyl ammonium iodide (4.12 g, 17 mmol) in dichloromethane (15 mL) was cooled to −78° C. and purged with nitrogen. Boron trichloride (1M in dichloromethane, 17 mL, 17 mmol) was added dropwise and the mixture was stirred for 15 minutes at −78° C. and at room temperature for 3 hours. The reaction mixture was quenched with water, stirred for 30 minutes and concentrated in vacuo. The aqueous residue was extracted with diethyl ether and the organic solution was washed with water (×5), dried over magnesium sulfate and concentrated in vacuo to afford the title compound as a brown solid in 91% yield, 826 mg. 1H NMR (400 MHz, CDCl3) δ: 2.20 (s, 3H), 7.10 (m, 1H), 7.20 (d, 1H), 10.10 (s, 1H); LRMS APCI m/z 132 [M−H]− purged with nitrogen The reaction mixture was quenched with water stirred for 30 minutes concentrated in vacuo The aqueous residue was extracted with diethyl ether the organic solution was washed with water (×5) dried over magnesium sulfate concentrated in vacuo
Source ID: ord-6b85009b092842f393f3104c2fa1013fConditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 3-methoxy-2-methylbenzonitrile [(1 g, 6.79 mmol) U.S. Pat. No. 5,965,766, p6] and tetra nbutyl ammonium iodide (4.12 g, 17 mmol) in dichloromethane (15 mL) was cooled to −78° C. and purged with nitrogen. Boron trichloride (1M in dichloromethane, 17 mL, 17 mmol) was added dropwise and the mixture was stirred for 15 minutes at −78° C. and at room temperature for 3 hours. The reaction mixture was quenched with water, stirred for 30 minutes and concentrated in vacuo. The aqueous residue was extracted with diethyl ether and the organic solution was washed with water (×5), dried over magnesium sulfate and concentrated in vacuo to afford the title compound as a brown solid in 91% yield, 826 mg. 1H NMR(400 MHz, CDCl3) δ: 2.20 (s, 3H), 7.10 (m, 1H), 7.20 (d, 1H), 10.10 (s, 1H); LRMS APCI m/z 132 [M−H]− purged with nitrogen The reaction mixture was quenched with water stirred for 30 minutes concentrated in vacuo The aqueous residue was extracted with diethyl ether the organic solution was washed with water (×5) dried over magnesium sulfate concentrated in vacuo
Source ID: ord-d321f6df14164a3a96d519f2d919818bPubChem References
These sources are listed in the compound's public database record.
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