반응 #814641

반응 방정식

sodium hydroxide

2-(hydroxymethyl)-5-t-butylphenol

2-t-butyl-4-methylphenol

hydrochloric acid

→

(2-hydroxy-3-t-butyl-5-methylphenyl)-(2-hydroxy-4-t-butylphenyl)methane

수율 36.0%

용매

water

water

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   온도This mixture was heated to a temperature of from 100° to 110° C.
3. 3
   workup.STIRRINGstirred at that temperature for 17.5 hours
4. 4
   추출extracted with ethyl acetate
5. 5
   세척The obtained ethyl acetate solution was washed with water
6. 6
   건조dried over anhydrous magnesium sulfate
7. 7
   기타removed
8. 8
   workup.DISTILLATIONethyl acetate was distilled off
9. 9
   기타the obtained residue was roughly separated by silica gel column chromatography
10. 10
    workup.ADDITIONTo the obtained brown highly viscous oil, n-hexane was added
11. 11
    workup.WAITleft

실험 절차

In a 300 ml eggplant-type flask equipped with a Dimroth condenser, 10.3 g (0.057 mol) of intermediate 2-(hydroxymethyl)-5-t-butylphenol and 10.2 g (0.062 mol) of 2-t-butyl-4-methylphenol were suspended in 60 ml of water. To this suspension, an aqueous solution having 10.2 g (0.26 mol) of sodium hydroxide dissolved in 50 ml of water, was added, and the mixture was stirred by a magnetic stirrer. This mixture was heated to a temperature of from 100° to 110° C. and stirred at that temperature for 17.5 hours. The reaction mixture was cooled to room temperature, acidified by concentrated hydrochloric acid and then extracted with ethyl acetate. The obtained ethyl acetate solution was washed with water and then dried over anhydrous magnesium sulfate. From the solution having the anhydrous magnesium sulfate removed, ethyl acetate was distilled off, and the obtained residue was roughly separated by silica gel column chromatography. To the obtained brown highly viscous oil, n-hexane was added and left to stand still to obtain 6.7 g (0.021 mol, yield: 36.0%) of (2-hydroxy-3-t-butyl-5-methylphenyl)-(2-hydroxy-4-t-butylphenyl)methane as a white solid. By 1HNMR, this solid was confirmed to be the desired product.

출처