HuagongsheHuagongshe Chemistry Print Report · For research reference only
Benzoic Acid → 2-[2-(4-Bromophenoxy)ethoxy]tetrahydro-2H-pyran
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Benzoic Acid | HCID 243 | — |
| Reactant | p-Toluenesulfonic acid | HCID 6101 | — |
| Reactant | 3,4-dihydro-2H-pyran | HCID 8080 | — |
| Reactant | 2-(p-Bromophenoxy)ethanol | HCID 99168 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 2-[2-(4-Bromophenoxy)ethoxy]tetrahydro-2H-pyran | HCID 12810473 | — |
Reaction Steps
The starting benzoic acid (I) is made by the reaction of 2-(4-bromophenoxy)ethanol (V) with dihydropyran, in the presence of methylene chloride and p-toluenesulfonic acid.H2O, to give 4-(2-tetrahydropyranyloxyethoxy)bromobenzene (VI). The bromobenzene (VI) is converted to 4-(2-tetrahydropyranyloxyethoxy)benzoic acid (VII) by reacting with magnesium, in tetrahydrofuran and dibromoethane, and then with carbon dioxide. Reaction of (VII) with methanol yields the starting benzoic acid (I). ##STR2##
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04304924 |
| Source dataset | uspto-grants-1981_12 |
| ORD ID | ord-2c9c154649684e9d9887963d5c835fe2 |
| Source note | uspto-grants-1981_12 |