Potassium Iodide → 2-[(5-Bromopentyl)oxy]benzaldehyde

A solution of salicylaldehyde (82 mmoles) in acetone (50 ml) was added dropwise to a refluxing solution of 1,5-dibromopentane (90.2 mmoles), potassium carbonate (90.2 mmoles) and potassium iodide (0.4 g) in acetone (200 ml). The mixture was refluxed for 18 hours, filtered and the filtrate concentrated. The residue was dissolved in ether and washed with cold 10% sodium hydroxide solution, water and brine. The organic layer was dried over magnesium sulfate and concentrated. The product was purified by flash chromatography (4% ethyl acetate/hexane) to give 2-(5-bromopentoxy)benzaldehyde. A mixture of this compound (11.1 mmoles), 4-acetyl-3-hydroxy-2-propyl phenol (11.62 mmoles) and potassium carbonate (5.55 mmoles) in acetone (30 ml) was refluxed for 5 days, stirred at room temperature for 2 days and then refluxed for 24 hours. The suspension was cooled to room temperature, filtered and the filtrate concentrated. The residue was dissolved in ethyl acetate and then washed with ice-cold 5% sodium hydroxide solution, water and brine. The dried solution was concentrated and the product flash chromatographed on silica gel and eluted with ethylacetate/hexane to give the desired product.

1. temperatureThe mixture was refluxed for 18 hours
2. filtrationfiltered
3. concentrationthe filtrate concentrated
4. dissolutionThe residue was dissolved in ether
5. washwashed with cold 10% sodium hydroxide solution, water and brine
6. dry with materialThe organic layer was dried over magnesium sulfate
7. concentrationconcentrated
8. customThe product was purified by flash chromatography (4% ethyl acetate/hexane)

ORD record

ord-a2ad2740fd084236923c8a7145a4ab61

Source dataset

uspto-grants-1989_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04871771