HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethyl Ether → Bis(p-dimethylaminophenyl)methoxyphenyl Acetic Acid, Methyl Ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethyl Ether | HCID 8254 | — |
| Reactant | 1,1,3,3-Tetramethylguanidine | HCID 66460 | — |
| Reactant | (+-)-Methyl mandelate | HCID 78066 | — |
| Reactant | 4,4'-Bis(dimethylamino)benzhydrol | HCID 92742 | — |
| Catalyst | Acetic Acid | HCID 176 | — |
| Catalyst | Methanesulfonic Acid | HCID 6395 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Hexane | HCID 8058 | — |
| Product | Bis(p-dimethylaminophenyl)methoxyphenyl Acetic Acid, Methyl Ester | HCID 131712797 | — |
Reaction Steps
A solution of methyl mandelate (97%, 6.44 g, 0.039 mole), 4,4'-bis(N,N'-dimethylamino)benzhydrol, methyl ether (11.0 g, 0.039 mole), 70 ml of tetrahydrofuran, 240 ml of n-hexane, 3 drops of methanesulfonic acid and 10 drops of acetic acid was refluxed for 6 hours, during which time an additional 200 ml of solvent was added. The volume was reduced to 200 ml, and decolorized with tetramethylguanidine and filtered hot. The filtrate was stripped, leaving a light blue clear oil. The oil was dissolved in toluene and chilled, yielding a white solid (2.8 g, mp 102°-105° C.).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04343939 |
| Source dataset | uspto-grants-1982_08 |
| ORD ID | ord-84f3807b5fe049629fbe4d6a9f565b56 |
| Source note | uspto-grants-1982_08 |