Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrogen Peroxide | HCID 784 | — |
| Reactant | Trimethyl borate | HCID 8470 | — |
| Reactant | HCID 3021210 | HCID 3021210 | — |
| Reactant | Magnesium | HCID 5462224 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 22982059 | HCID 22982059 | 69% |
Reaction Steps
A Grignard reagent was previously prepared using 99.3 g of 1-tert-amyloxy-4-chlorobenzene, 12.76 g of magnesium, and 200 mL of tetrahydrofuran. To the Grignard reagent, 57.1 g of trimethyl borate was added dropwise at an internal temperature below −50° C. At a reaction temperature of 5° C., stirring was continued for 3 hours. Thereafter, at an internal temperature below 30° C., 45.0 g of acetic acid and 145.7 g of 35% hydrogen peroxide solution were added. At room temperature, stirring was continued for 3 hours. Standard work-up and purification by silica gel chromatography gave 62.2 g of 4-tert-amyloxy-1-phenol (yield 69%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09017918B2 |
|---|
| Source dataset | uspto-grants-2015_04 |
|---|
| ORD ID | ord-d919bfed7dc04e7fa2ace3de1c2659db |
|---|
| Source note | uspto-grants-2015_04 |
|---|