Dichloromethane → 2-Methyl-2-adamantanol

HRID 325120

Reaction equation

HRID 325120 reaction equation
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

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 64151AdamantanoneHCID 178418573HCID 178418573, compound

Product 1

HCID 1365452-Methyl-2-adamantanolYield 80%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-e0229c0964154a90b611bc7fdebb00f5
Source dataset
uspto-grants-2001_04
Patent number
US06222061B1

Linked notes

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