3-Chloro-2-methyl-1-propene → alpha-Methallyl-alpha,3,3-trimethyl-5-norbornene-2-methanol

HRID 2163643Notes

Reaction equation

HRID 2163643 reaction equation
[Mg].[CH2:2](Cl)[C:3](=[CH2:5])[CH3:4].[C:7]([CH:10]1[C:15]([CH3:17])([CH3:16])[CH:14]2[CH2:18][CH:11]1[CH:12]=[CH:13]2)(=[O:9])[CH3:8].[Cl-].[NH4+]>C(OCC)C>[CH2:2]([C:7]([CH3:8])([CH:10]1[C:15]([CH3:16])([CH3:17])[CH:14]2[CH2:18][CH:11]1[CH:12]=[CH:13]2)[OH:9])[C:3](=[CH2:5])[CH3:4]

Participants

6

Reactant 4

HCID 112413-Chloro-2-methyl-1-propeneHCID 25517Ammonium ChlorideHCID 1625111-(3,3-Dimethylbicyclo(2.2.1)hept-5-en-2-yl)ethan-1-oneHCID 5462224Magnesium

Product 1

HCID 21319801alpha-Methallyl-alpha,3,3-trimethyl-5-norbornene-2-methanolYield 106.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Into a 1 liter reaction flask equipped with a reflux condenser, thermometer, stirrer, dropping funnel and nitrogen inlet tube are placed 12 g (0.5 moles) of magnesium turnings and 250 cc anhydrous diethyl ether. Over a 2 hour period, 45.3 g (0.5 moles) of methallyl chloride is added. The Grignard solution is stirred for 1/2 hour and 28 g of 2-acetyl-3,3-dimethyl-5-norbornene is added over a 20 minute period. The mixture is stirred at reflux for 1/2 hour and then is hydrolyzed by the addition of saturated ammonium chloride solution. The organic layer is washed with water and dried over magnesium sulfate. The mixture is then filtered and the solvent evaporated to yield 40 g of an oil, which is then fractionated on a micro Vigreux column after adding thereto 5 g Primol® and a trace quantity of Ionox®.

Workup

  1. customInto a 1 liter reaction flask
  2. customequipped with a reflux condenser
  3. customthermometer, stirrer, dropping
  4. customfunnel and nitrogen inlet tube are placed
  5. stirringThe mixture is stirred
  6. temperatureat reflux for 1/2 hour
  7. washThe organic layer is washed with water
  8. dry with materialdried over magnesium sulfate
  9. filtrationThe mixture is then filtered
  10. customthe solvent evaporated

Sources & evidence

ORD record
ord-ed15bcdea745481f8b9e2b79615d79e3
Source dataset
uspto-grants-1979_01
Patent number
US04136120

Reaction notes

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