반응 #527391

반응 방정식

sodium hydrogen carbonate

(2S,3R)-2-octyl-1,3-butanediol

p-hydroxybenzaldehyde

sulfuric acid

sodium hydrogen carbonate

→

4-[(2S,4R,5S)-5-octyl-4-methyl-1,3-dioxan-2-yl]phenol

수율 84.7%

용매

diethyl ether

toluene

diethyl ether

water

반응 조건

후처리

1. 1
   기타was placed under nitrogen in a round flask
2. 2
   온도The mixture was heated
3. 3
   온도to reflux for 3 hours
4. 4
   기타while separating water
5. 5
   기타The cooled reaction mixture
6. 6
   기타The aqueous phase was separated
7. 7
   추출extracted three times with diethyl ether
8. 8
   세척The combined organic phases were washed three times with round flask
9. 9
   온도The mixture was heated
10. 10
    온도to reflux for 3 hours
11. 11
    기타while separating water
12. 12
    기타The cooled reaction mixture
13. 13
    기타The aqueous phase was separated
14. 14
    추출extracted three times with diethyl ether
15. 15
    세척The combined organic phases were washed three times with water
16. 16
    건조dried over magnesium sulfate
17. 17
    여과filtered
18. 18
    기타evaporated
19. 19
    기타Recrystallization of the yellowish, solid residue (480 mg) from hexane/ethyl acetate (vol. 25:1)

실험 절차

A mixture of 320 mg of (2S,3R)-2-octyl-1,3-butanediol, 193 mg of p-hydroxybenzaldehyde, 0.1 ml of 1N sulfuric acid and 20 ml of toluene was placed under nitrogen in a round flask having a magnetic stirrer, water separator and condenser. The mixture was heated to reflux for 3 hours while separating water. The cooled reaction mixture was poured into aqueous sodium hydrogen carbonate solution and treated with diethyl ether. The aqueous phase was separated and extracted three times with diethyl ether. The combined organic phases were washed three times with round flask having a magnetic stirrer, water separator and condenser. The mixture was heated to reflux for 3 hours while separating water. The cooled reaction mixture was poured into aqueous sodium hydrogen carbonate solution and treated with diethyl ether. The aqueous phase was separated and extracted three times with diethyl ether. The combined organic phases were washed three times with water, dried over magnesium sulfate, filtered and evaporated. Recrystallization of the yellowish, solid residue (480 mg) from hexane/ethyl acetate (vol. 25:1) gave 410 mg of 4-[(2S,4R,5S)-5-octyl-4-methyl-1,3-dioxan-2-yl]phenol as yellowish crystals with [a]D =+27° (c=1% in chloroform).

출처