Reaktion #4789

Reaktionsgleichung

formaldehyde

sodium hydroxide

4-tert-butylphenol

hydrochloric acid

phenol

→

4-tert-butyl-2,6-di(hydroxymethyl)phenol

Lösungsmittel

chloroform

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISSOLUTIONdissolved
2. 2
   workup.STIRRINGthe solution was stirred for four to six days at ambient temperature
3. 3
   SonstigeA yellow, oily organic phase was isolated
4. 4
   Waschenwashed with three 500 ml portions of water
5. 5
   workup.ADDITIONChloroform (700 ml) and 500 ml of water were added to this organic oil
6. 6
   workup.STIRRINGthe mixture was stirred
7. 7
   SonstigeThe organic phase was isolated
8. 8
   Trocknendried over 100 g of anhydrous magnesium sulphate
9. 9
   SonstigeEvaporation
10. 10
    Temperaturcooling of the chloroform solution
11. 11
    Sonstigeyielded
12. 12
    workup.ADDITIONa mixture of white crystals and oil

Vorschrift

50 g sodium hydroxide were dissolved in approximately 1.2 liters of water, and 150 g of 4-tert-butylphenol were added to this solution. The mixture was stirred and gently heated until the phenol dissolved. The solution was then cooled to ambient temperature. Aqueous formaldehyde (175 ml, 37 percent) was added, and the solution was stirred for four to six days at ambient temperature. Concentrated hydrochloric acid (110 ml) was added, upon which a two-phase system forms. A yellow, oily organic phase was isolated and washed with three 500 ml portions of water. Chloroform (700 ml) and 500 ml of water were added to this organic oil and the mixture was stirred. The organic phase was isolated and dried over 100 g of anhydrous magnesium sulphate. Evaporation and cooling of the chloroform solution yielded a mixture of white crystals and oil. The addition of 50-100 ml of chloroform and filtration yielded a white crystalline product, 4-tert-butyl-2,6-di(hydroxymethyl)phenol.

Quelle