HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → 1-(Cyclohexylidene(4-methoxyphenyl)methyl)-4-methoxybenzene
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | 4-Bromoanisole | HCID 7730 | — |
| Reactant | Methyl cyclohexanecarboxylate | HCID 20748 | — |
| Product | 1-(Cyclohexylidene(4-methoxyphenyl)methyl)-4-methoxybenzene | HCID 82458 | — |
Reaction Steps
The Grignard reaction of p-bromoanisole (15.0 g, 0.080 mol) and methyl cyclohexane carboxylate (Compound 26) (5.7 g, 0.040 mol) afforded the carbinol (Compound 27) which upon dehydration yielded a yellow solid. Recrystallized from absolute EtOH yielded 8.0 g (65%) of a colorless solid, mp 106°-107° C. (MIQUEL, J -F., WAHLSTAM, H., OLSSON, K. AND SUNDBECK, B. (1963), "Synthesis of unsymmetrical diphenylalkenes", Journal of Medicinal Chemistry, 6, 774), 109°-110° C. 1H NMR (CDCl3) δ 1.70 (broad s, 10H, cyclohexyl), 3.70 (s, 6H, OCH3), 7.07 (dd, 8H, ArH).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05397802 |
| Source dataset | uspto-grants-1995_03 |
| ORD ID | ord-e194a98366e84cecbd2913f84873bb12 |
| Source note | uspto-grants-1995_03 |