HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Hydroxybenzaldehyde → 4-[2-(5-Ethyl-2-pyridinyl)-2-hydroxyethoxy]benzaldehyde
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Hydroxybenzaldehyde | HCID 126 | — |
| Reactant | N-bromobutanimide | HCID 67184 | — |
| Reactant | Pyridine, 5-ethyl-2-vinyl- | HCID 222462 | — |
| Reactant | Potassium | HCID 5462222 | — |
| Solvent | tert-Butanol | HCID 6386 | — |
| Product | 4-[2-(5-Ethyl-2-pyridinyl)-2-hydroxyethoxy]benzaldehyde | HCID 11550787 | 79% |
Reaction Steps
To a solution of 5 g (0.03759 mol) 5-ethyl-2-vinyl-pyridine dissolved in 75 mL of 25% aqueous tertiary butanol added 8.02 g (0.045 mol) N-bromosuccinimide at 25-30° C. in 30 min. Reaction mixture was stirred for 2 hr. The progress of reaction was monitored by TLC and after complete consumption of the 5-ethyl-2-vinyl-pyridine, 6.01 g (0.03759 mol) potassium salt of 4-hydroxy benzaldehyde was added. Reaction mixture was stirred for 18 hr. at 75-80° C. Subsequent work-up in water and extraction with ethyl acetate yielded 8.04 g (79%) of the titled product. m.p. 81° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08173816B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-1550ce52a1a74bad800d1632ab0fbdf6 |
| Source note | uspto-grants-2012_05 |