Water → 3,3',5,5'-Tetramethyl-1,1'-biadamantane

HRID 41286

Reaction equation

HRID 41286 reaction equation
[Na].Br[C:3]12[CH2:12][C:7]3([CH3:13])[CH2:8][CH:9]([CH2:11][C:5]([CH3:14])([CH2:6]3)[CH2:4]1)[CH2:10]2.O>CCCCCCCC>[CH3:9][C:3]12[CH2:10][CH:9]3[CH2:8][C:7]([CH3:13])([CH2:6][C:5]([C:14]45[CH2:14][C:5]6([CH3:11])[CH2:4][CH:3]([CH2:12][C:7]([CH3:13])([CH2:6]6)[CH2:8]4)[CH2:10]5)([CH2:11]3)[CH2:4]1)[CH2:12]2

Participants

5

Reactant 3

HCID 962WaterHCID 983171-Bromo-3,5-dimethyladamantaneHCID 5360545Sodium

Product 1

HCID 235969703,3',5,5'-Tetramethyl-1,1'-biadamantaneYield 159.6%

Reagents, catalysts & solvents 1

HCID 356OctaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A four-neck 1000 ml flask provided with a thermometer, stirrer, and reflux tube was charged with metal sodium 14 g (0.6 mol) and n-octane 600 ml and was cooled to an inside temperature of 0° C. While vigorously stirring, 1-bromo-3,5-dimethyl adamantane 73.0 g (0.3 mol) previously dissolved in n-octane 300 ml was gradually added dropwise. While dropping, the inside temperature was kept at 0° C. to 5° C. After the end of the dropwise addition, when the temperature no longer rose, the reaction was continued for 1 hour. After that, the reactant was poured into cold water 1500 ml, then the crude product was separated by filtration, rinsed with pure water, and dried. Further, the crude product was recrystallized by hot hexane. The obtained recrystallized product was dried under reduced pressure to obtain the product 78.2 g.

Workup

  1. customA four-neck 1000 ml flask provided with a thermometer, stirrer
  2. temperaturereflux tube
  3. additionwas gradually added dropwise
  4. customwas kept at 0° C. to 5° C
  5. additionAfter the end of the dropwise addition, when the temperature
  6. customthe crude product was separated by filtration
  7. washrinsed with pure water
  8. customdried
  9. customFurther, the crude product was recrystallized by hot hexane
  10. customThe obtained recrystallized product
  11. customwas dried under reduced pressure

Sources & evidence

ORD record
ord-29504958b2a54a12b5bf7be1d21503ea
Source dataset
uspto-grants-2013_09
Patent number
US08530596B2

Linked notes

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