Adamantanone → Magnesium Bromide

HRID 1790864Notes

Reaction equation

HRID 1790864 reaction equation
[CH3:1][Mg:2][Br:3].[Cl-].[Ca+2].[Cl-].[CH:7]12[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][CH:9]([CH2:10]3)[C:8]1=[O:17])[CH2:14]2>O1CCCC1>[Br-:3].[Mg+2:2].[Br-:3].[CH3:1][C:8]1([OH:17])[CH:9]2[CH2:15][CH:13]3[CH2:12][CH:11]([CH2:16][CH:7]1[CH2:14]3)[CH2:10]2

Participants

6

Reactant 3

HCID 64151AdamantanoneHCID 5284359Calcium ChlorideHCID 178418573HCID 178418573, compound

Product 2

HCID 82241Magnesium BromideHCID 1365452-Methyl-2-adamantanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

44 ml of a tetrahydrofuran solution containing 0.06 mole of methyl magnesium bromide was added into a 200-ml four-necked flask provided with a stirrer and a drying tube filled with calcium chloride. There to was dropwise added, at room temperature in a nitrogen atmosphere, a solution of 7.5 g (0.05 mole) of 2-adamantanone dissolved in 30 ml of tetrahydrofuran, with the temperature of the mixture in the flask being controlled so as not to exceed 40° C. After the completion of the dropwise addition, the mixture was stirred at 50° C. for 3 hours. The proceeding of a reaction was confirmed by GC. As a result, magnesium bromide salt of 2-methyl-2-adamantanol was formed by nearly 100%.

Workup

  1. additionwas added into a 200-ml four-necked flask
  2. customprovided with a stirrer and a drying tube
  3. additionThere to was dropwise added, at room temperature in a nitrogen atmosphere
  4. customto exceed 40° C
  5. additionAfter the completion of the dropwise addition

Sources & evidence

ORD record
ord-027d4c7cc0c844d4951bbb55fc5019b0
Source dataset
uspto-grants-2006_07
Patent number
US07071352B2

Reaction notes

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