HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → 2-Methyl-2-phenyl-6-bromohexanol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Lithium borohydride | HCID 4148881 | — |
| Reactant | Ethyl 6-bromo-2-methyl-2-phenylhexanoate | HCID 11174430 | — |
| Reactant | 6-Bromo-2-methyl-2-p-tolylhexan-1-ol | HCID 11196892 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 2-Methyl-2-phenyl-6-bromohexanol | HCID 11300228 | 84% |
Reaction Steps
According to the procedure given for the synthesis of 206e, 205d (52.0 g, 166.0 mmol) was reacted with LiBH4 (5.4 g, 247.9 mmol) and methanol (8.2 g, 255.9 mmol) in CH2Cl2 (180 mL) to afford 206d (38.0 g, 84%) as an oil. 1H NMR (CDCl3): δ 7.5-7.1 (m, 5 H), 3.60 (d, 1 H, J=10.8), 3.53 (d, 1 H, J=10.8), 3.34 (t, 2 H, J=7.0), 1.90-1.78 (m, 3 H), 1.62-1.26 (m, 3 H), 1.35 (s, 3 H), 1.14 (m, 1 H). 13C NMR (CDCl3): δ 144.4, 128.4, 126.5, 126.1, 72.4, 43.2, 37.4, 33.5, 33.3, 22.5, 21.4.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08642653B2 |
| Source dataset | uspto-grants-2014_02 |
| ORD ID | ord-ddeee37e076e4c10b2df2e93e226ee67 |
| Source note | uspto-grants-2014_02 |