4,6-Dimethoxysalicylaldehyde → 3,5-Dimethoxy-2-propylphenol

Triphenylphosphine ethylbromide (4.1 g) was added to a 2N sodium hydride/dimethyl sulfoxide solution (11 ml), prior to agitation at 50° C. for 30 minutes. To the mixture was added 4,6-dimethoxy-2-hydroxybenzaldehyde (1 g), for agitation at 50° C. overnight. After the termination of the reaction, the resulting solution was partitioned with ethyl acetate and dilute hydrochloric acid, and the resulting ethyl acetate phase was washed in water and subsequently in a saturated sodium chloride solution and dried over anhydrous magnesium sulfate, to distill off the solvents under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: hexane:ethyl acetate=3:1), followed by addition of a catalytic amount of platinum dioxide for hydrogenation, to recover 3,5-dimethoxy-2-propylphenol (0.5 g; yield of 46%). By 1H-NMR (90 MHz, CDCl3), the compound has the peaks shown below.

1. customat 50° C.
2. customovernight
3. customAfter the termination of the reaction
4. customthe resulting solution was partitioned with ethyl acetate and dilute hydrochloric acid
5. washthe resulting ethyl acetate phase was washed in water and subsequently in a saturated sodium chloride solution
6. dry with materialdried over anhydrous magnesium sulfate
7. distillationto distill off the solvents under reduced pressure
8. customThe residue was purified by silica gel column chromatography (developing solvent: hexane:ethyl acetate=3:1)
9. additionfollowed by addition of a catalytic amount of platinum dioxide for hydrogenation

ORD-Eintrag

ord-5b95cd72edf0492b9e7ff218eee8d726

Quelldatensatz

uspto-grants-1998_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05734067