HuagongsheHuagongshe Chemistry Print Report · For research reference only
3,4-dihydro-2H-pyran → 3-(((2-Tetrahydropyranyl)oxy)methyl)benzaldehyde
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3,4-dihydro-2H-pyran | HCID 8080 | — |
| Reactant | Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) | HCID 466102 | — |
| Reactant | Ammonium Acetate | HCID 517165 | — |
| Reactant | 3-(Hydroxymethyl)benzaldehyde | HCID 13131455 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 3-(((2-Tetrahydropyranyl)oxy)methyl)benzaldehyde | HCID 19002937 | — |
Reaction Steps
To the alcohol of Step 1 (94 g) in CH2Cl2 (1.5 L) at 0° C. was added 3,4-dihydro-2H-pyran (300 mL) followed by pyridinium p-toluenesulfonate (5.0 g). After 3 hours at room temperature, the reaction mixture was poured on aqueous 25% ammonium acetate and extracted with CH2Cl2. The resulting mixture was purified by flash chromatography (50% EtOAc in toluene) to give 147 g of the title aldehyde.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05438141 |
| Source dataset | uspto-grants-1995_08 |
| ORD ID | ord-24725498daac4dffa10b22db9532a20b |
| Source note | uspto-grants-1995_08 |