Diethyl Ether → 3,3',5,5'-Tetramethyl-1,1'-biadamantane

HRID 2195583Notes

Reaction equation

HRID 2195583 reaction equation
[Mg].C(O[CH2:5][CH3:6])C.[CH3:7][C:8]12[CH2:18][CH:12]3[CH2:13][C:14]([CH3:17])([CH2:16][C:10](Br)([CH2:11]3)[CH2:9]1)[CH2:15]2>ClCCl.O>[CH3:7][C:8]12[CH2:18][CH:12]3[CH2:13][C:14]([CH3:17])([CH2:16][C:10]([C:14]45[CH2:15][C:8]6([CH3:18])[CH2:9][CH:10]([CH2:11][C:5]([CH3:6])([CH2:7]6)[CH2:13]4)[CH2:16]5)([CH2:11]3)[CH2:9]1)[CH2:15]2

Participants

6

Reactant 3

HCID 3283Diethyl Ether3×HCID 983171-Bromo-3,5-dimethyladamantane2×HCID 5462224Magnesium

Product 1

HCID 235969703,3',5,5'-Tetramethyl-1,1'-biadamantaneYield 47%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Into a 2 liter egg plant-shaped flask, 9.8 g (0.4 moles) of magnesium was weighed and placed. Under the stream of nitrogen gas, 80 ml of diethyl ether was added and stirred. Then, a solution prepared by dissolving 97.28 g (0.4 moles) of 3,5-dimethyl-1-bromoadamantane into 40 ml of diethyl ether was added dropwise. After the addition was completed, the resultant mixture was heated under the refluxing condition for 30 minutes. The temperature was adjusted at the room temperature, and diethyl ether was completely removed using a vacuum pump. Then, a solution prepared by dissolving 48.64 g (0.2 moles) of 3,5-dimethyl-1-bromoadamantane into 600 ml of dichloromethane was added dropwise. After the addition was completed, the resultant mixture was heated under the refluxing condition for 5 hours. The reaction fluid was poured into 400 ml of ion-exchanged water and treated by extraction with dichloromethane using a separation funnel. The solvent was removed using an evaporator. The residue was dissolved into 40 ml of hexane and purified in accordance with the silica gel column chromatography (the solvent of development: hexane). The solvent was removed using an evaporator, and 30.70 g of 3,3′,5,5′-tetramethyl-1,1′-biadamantane was obtained (the yield: 47%). Since the molecular weight was 327 in the mass analysis, it was shown that the product was the object compound.

Workup

  1. customThen, a solution prepared
  2. additionwas added dropwise
  3. additionAfter the addition
  4. customwas completely removed
  5. customThen, a solution prepared
  6. additionwas added dropwise
  7. additionAfter the addition
  8. customThe solvent was removed
  9. customan evaporator
  10. dissolutionThe residue was dissolved into 40 ml of hexane
  11. custompurified in accordance with the silica gel column chromatography (the solvent of development
  12. customThe solvent was removed
  13. customan evaporator

Sources & evidence

ORD record
ord-74cbc2a2b40e4216b201ae37d7129bf4
Source dataset
uspto-grants-2012_12
Patent number
US08337982B2

Reaction notes

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