Dichloromethane → 2-Methyl-2-adamantanol

HRID 325120

Reaktionsgleichung

Reaktionsgleichung von HRID 325120
C[Mg]Br.[CH:4]12[CH2:13][CH:8]3[CH2:9][CH:10]([CH2:12][CH:6]([CH2:7]3)[C:5]1=[O:14])[CH2:11]2.[CH2:15](Cl)Cl>C(OCC)C.O1CCCC1>[CH3:15][C:5]1([OH:14])[CH:6]2[CH2:12][CH:10]3[CH2:9][CH:8]([CH2:13][CH:4]1[CH2:11]3)[CH2:7]2

Komponenten

6

Edukt 3

HCID 6344DichloromethaneHCID 64151AdamantanoneHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 1365452-Methyl-2-adamantanolAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

110 ml of a solution of methyl magnesium bromide (3.0 M) in diethyl ether was diluted with 100 ml of anhydrous tetrahydrofuran (THF). Then, the solution was put into a 1 liter flask and then maintained at 0° C. 2-adamantanone (45 g, 0.3 mol) was dropped slowly using a dropping funnel and then the reaction was stirred at room temperature for about 12 hours. After completion of the reaction, excess THF was removed using a rotary evaporator and then the resultant product was poured into water. Then, the resultant product was neutralized with dilute sulfuric acid and extracted using diethyl ether and was then dried over magnesium sulfate. The obtained crude product was recrystallized using n-hexane and a methylene chloride cosolvent to yield the desired product 2-methyl-2-adamantanol (yield: 80%).

Aufarbeitung

  1. customThen, the solution was put into a 1 liter flask
  2. customwas removed
  3. customa rotary evaporator
  4. additionthe resultant product was poured into water
  5. extractionextracted
  6. dry with materialwas then dried over magnesium sulfate
  7. customThe obtained crude product
  8. customwas recrystallized

Quellen und Nachweise

ORD-Eintrag
ord-e0229c0964154a90b611bc7fdebb00f5
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06222061B1

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