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CC(C)(C)OC1=CC=C(C=C1)OChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 4-[(2-methylpropan-2-yl)oxy]phenol |
|---|---|
| IUPAC Name | — |
| CAS Number | 2460-87-9 |
| Database ID | 2773621 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
4-[(2-methylpropan-2-yl)oxy]phenol (CAS 2460-87-9) 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 2773621
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-e7a058453f9642d1a4f7dc950af56171Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-f37baeb53d824146ba595804ea95e511Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of KOH (0.224 g, 4 mmol) in MeOH (3 mL) was added, over the course of 30 min, to a warmed (70° C.) mixture of 1,2-dibromoethane (3 g, 0.016 mol) and 4-(tert-butoxy)phenol (0.66 g, 0.004 mol). The mixture was stirred at 70° C. for 15 h before water and CHCl3 were added. The layers were separated, the organic layer washed with 10% aqueous NaOH and then dried (Na2SO4) and concentrated in vacuo to give 0.32 g (28%) of the sub-title compound. to a warmed were added The layers were separated the organic layer washed with 10% aqueous NaOH dried (Na2SO4) concentrated in vacuo
Source ID: ord-8c37cc22ff5b42abadd97079f22480d0Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Sec-butyllithium (53.2 mmoles, 41 ml of 1.3M in hexane) was added dropwise at -78° C. to 4-bromo-t-butoxybenzene (53.2 mmoles, 12.2 g) in 200 ml THF, stirred at -78° C. for 1 hour, and added slowly to a solution of triisopropylborate (58.5 mmoles, 11.0g) in 50 ml THF while maintaining the temperature below -60° C. The mixture was allowed to warm gradually to -20° C. Chilled acetic acid (80 mmoles,9.6 ml) was added. Hydrogen peroxide (58.5 mmoles, 5.9 ml of 30% diluted with 5 ml water) was added dropwise over 15 minutes while maintaining the temperature below 0° C. After stirring 10 minutes, the solution was washed with ammonium sulfate solution, dried, and concentrated. The residue was triturated with hexane and filtered to yield 4.2 g of 4-t-butoxyphenol. (MS). while maintaining the temperature below -60° C to warm gradually to -20° C while maintaining the temperature below 0° C After stirring 10 minutes the solution was washed with ammonium sulfate solution dried concentrated The residue was triturated with hexane filtered
Source ID: ord-015a1be4b3c34c43ba71af8e2af51c08Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-e7a058453f9642d1a4f7dc950af56171Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-e7a058453f9642d1a4f7dc950af56171Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Sec-butyllithium (53.2 mmoles, 41 ml of 1.3M in hexane) was added dropwise at -78° C. to 4-bromo-t-butoxybenzene (53.2 mmoles, 12.2 g) in 200 ml THF, stirred at -78° C. for 1 hour, and added slowly to a solution of triisopropylborate (58.5 mmoles, 11.0g) in 50 ml THF while maintaining the temperature below -60° C. The mixture was allowed to warm gradually to -20° C. Chilled acetic acid (80 mmoles,9.6 ml) was added. Hydrogen peroxide (58.5 moles, 5.9 ml of 30% diluted with 5 ml water) was added dropwise over 15 minutes while maintaining the temperature below 0° C. After stirring 10 minutes, the solution was washed with ammonium sulfate solution, dried, and concentrated. The residue was triturated with hexane and filtered to yield 4.2 g of 4-t-butoxyphenol. (MS). while maintaining the temperature below -60° C to warm gradually to -20° C while maintaining the temperature below 0° C After stirring 10 minutes the solution was washed with ammonium sulfate solution dried concentrated The residue was triturated with hexane filtered
Source ID: ord-9bd3c5f599074db2bdd22327ce9533b1Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of KOH (0.224 g, 4 mmol) in MeOH (3 mL) was added, over the course of 30 min, to a warmed (70° C.) mixture of 1,2-dibromoethane (3 g, 0.016 mol) and 4-(tert-butoxy)phenol (0.66 g, 0.004 mol). The mixture was stirred at 70° C. for 15 h before water and CHCl3 were added. The layers were separated, the organic layer washed with 10% aqueous NaOH and then dried (Na2SO4) and concentrated in vacuo to give 0.32 g (28%) of the sub-title compound. to a warmed were added The layers were separated the organic layer washed with 10% aqueous NaOH dried (Na2SO4) concentrated in vacuo
Source ID: ord-088ac04fbafa4314b410de126c821beaConditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Sec-butyllithium (53.2 mmoles, 41 ml of 1.3M in hexane) was added dropwise at -78° C. to 4-bromo-t-butoxybenzene (53.2 mmoles, 12.2 g) in 200 ml THF, stirred at -78° C. for 1 hour, and added slowly to a solution of triisopropylborate (58.5 mmoles, 11.0 g) in 50 ml THF while maintaining the temperature below -60° C. The mixture was allowed to warm gradually to -20° C. Chilled acetic acid (80 mmoles,9.6 ml) was added. Hydrogen peroxide (58.5 moles, 5.9 ml of 30% diluted with 5 ml water) was added dropwise over 15 minutes while maintaining the temperature below 0° C. After stirring 10 minutes, the solution was washed with ammonium sulfate solution, dried, and concentrated. The residue was triturated with hexane and filtered to yield 4.2 g of 4-t-butoxyphenol. (MS). while maintaining the temperature below -60° C to warm gradually to -20° C while maintaining the temperature below 0° C After stirring 10 minutes the solution was washed with ammonium sulfate solution dried concentrated The residue was triturated with hexane filtered
Source ID: ord-f4b602b2e89840d0bb45e91d9bd93298Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Sec-butyllithium (53.2 mmoles, 41 ml of 1.3M in hexane) was added dropwise at -78° C. to 4-bromo-t-butoxybenzene (53.2 mmoles, 12.2 g) in 200 ml THF, stirred at -78° C. for 1 hour, and added slowly to a solution of triisopropylborate (58.5 mmoles, 11.0g) in 50 ml THF while maintaining the temperature below -60° C. The mixture was allowed to warm gradually to -20° C. Chilled acetic acid (80 mmoles,9.6 ml) was added. Hydrogen peroxide (58.5 mmoles, 5.9 ml of 30% diluted with 5 ml water) was added dropwise over 15 minutes while maintaining the temperature below 0° C. After stirring 10 minutes, the solution was washed with ammonium sulfate solution, dried, and concentrated. The residue was triturated with hexane and filtered to yield 4.2 g of 4-t-butoxyphenol. (MS). while maintaining the temperature below -60° C to warm gradually to -20° C while maintaining the temperature below 0° C After stirring 10 minutes the solution was washed with ammonium sulfate solution dried concentrated The residue was triturated with hexane filtered
Source ID: ord-92f500cf55b643f0bd171d94cdcf171aConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 4-Tert-butoxyphenol (200 mg, 1.203 mmole) and PPh3 (410 mg, 1.564 mmole) were combined in toluene (5 mL). To this was added tetrahydro-2H-pyran-4-ol (0.149 mL, 1.564 mmole). DIAD (0.304 mL, 1.564 mmole) was added dropwise at RT. After stirring overnight the mixture was concentrated. Flash column chromatography (Biotage-SNAP-25 g SiO2, 10% EtOAc/hexanes) gave 4-(4-tert-butoxyphenoxy)tetrahydro-2H-pyran (257 mg, 85%) as a clear oil. 1H NMR (400 MHz, CDCl3): 06.90 (d, J=8.9 Hz, 2 H); 6.83-6.79 (m, 2 H); 4.39 (m, 1 H); 4.03-3.95 (m, 2 H); 3.56 (m, 2 H); 2.04-1.96 (m, 2 H); 1.83-1.72 (m, 2 H); 1.30 (s, 9 H). was concentrated
Source ID: ord-a01ef0f946434be3bc9474f507c3c7e9Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 4-Tert-butoxyphenol (200 mg, 1.203 mmole) and PPh3 (410 mg, 1.564 mmole) were combined in toluene (5 mL). To this was added tetrahydro-2H-pyran-4-ol (0.149 mL, 1.564 mmole). DIAD (0.304 mL, 1.564 mmole) was added dropwise at RT. After stirring overnight the mixture was concentrated. Flash column chromatography (Biotage-SNAP-25 g SiO2, 10% EtOAc/hexanes) gave 4-(4-tert-butoxyphenoxy)tetrahydro-2H-pyran (257 mg, 85%) as a clear oil. 1H NMR (400 MHz, CDCl3): 06.90 (d, J=8.9 Hz, 2 H); 6.83-6.79 (m, 2 H); 4.39 (m, 1 H); 4.03-3.95 (m, 2 H); 3.56 (m, 2 H); 2.04-1.96 (m, 2 H); 1.83-1.72 (m, 2 H); 1.30 (s, 9 H). was concentrated
Source ID: ord-a01ef0f946434be3bc9474f507c3c7e9PubChem References
These sources are listed in the compound's public database record.
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