HuagongsheHuagongshe Chemistry Print Report · For research reference only
Iodine → 2,5-Bis-hydroxymethyl-2,3-dihydrobenzofuran
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Iodine | HCID 807 | — |
| Reactant | Ethyl 2-hydroxymethyl-2,3-dihydrobenzofuran-5-carboxylate | HCID 13728720 | — |
| Reactant | Ethyl 2-methoxymethyl-2,3-dihydrobenzofuran-5-carboxylate | HCID 20163636 | — |
| Reactant | Aluminium lithium hydride | HCID 21226445 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl acetate hexane | HCID 21226206 | — |
| Product | 2,5-Bis-hydroxymethyl-2,3-dihydrobenzofuran | HCID 20163652 | 83.2% |
Reaction Steps
Reduction of 444 mg (2 mmole) ethyl 2-hydroxymethyl-2,3-dihydrobenzofuran-5-carboxylate, Preparation A, Part (iii), in 15 ml tetrahydrofuran with lithium aluminum hydride, 155 mg (4 mmole), by the method of Preparation A, Part iv), afforded 0.3 g of 2,5-bis-hydroxymethyl-2,3-dihydrobenzofuran as an oil, TLC 1:2 ethyl acetate/hexane, Rf 0.2, iodine positive. 1H-NMR(CDCl3)ppm(delta): 3.6 (CH2OH at 2-position), 4.6 (CH2OH at 5-position).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04703052 |
| Source dataset | uspto-grants-1987_10 |
| ORD ID | ord-cd4ae05e074a4a5b937c96b22bc646aa |
| Source note | uspto-grants-1987_10 |