반응 #3782

반응 방정식

potassium tert-butoxide

triphenylphosphine ethyl bromide

2,6-dimethoxy-4-hydroxybenzaldehyde

→

3,5-dimethoxy-4-propylphenol

수율 55.7%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.STIRRINGfor stirring at room temperature for 30 minutes
2. 2
   workup.STIRRINGfor stirring at room temperature for 2 hours
3. 3
   기타After the termination of the reaction
4. 4
   기타the resulting solution was partitioned with ethyl acetate and dilute hydrochloric acid
5. 5
   세척the resulting ethyl acetate phase was washed in water and subsequently in a saturated sodium chloride solution
6. 6
   건조dried over anhydrous magnesium sulfate
7. 7
   workup.DISTILLATIONto distill off the solvents under reduced pressure
8. 8
   기타The residue was purified by silica gel column chromatography (developing solvent: hexane:ethyl acetate=2:1)
9. 9
   workup.ADDITIONfollowed by addition of a catalytic amount of platinum dioxide for hydrogenation

실험 절차

Anhydrous tetrahydrofuran (36 ml) was added to triphenylphosphine ethyl bromide (12.3 g) prior to stirring at room temperature for 20 minutes. To the resulting mixture was added potassium tert-butoxide (4.5 g), for stirring at room temperature for 30 minutes. Then, 2,6-dimethoxy-4-hydroxybenzaldehyde (3.0 g) was added to the resulting mixture for stirring at room temperature for 2 hours. 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=2:1), followed by addition of a catalytic amount of platinum dioxide for hydrogenation, to recover 3,5-dimethoxy-4-propylphenol (1.8 g; yield of 55%). By 1H-NMR (90 MHz, CDCl3), the compound has the peaks shown below.

출처