Sulfuric Acid → 2-Methylideneadamantane

HRID 858912

Reaction equation

HRID 858912 reaction equation
[CH3:1][C:2]1(O)[CH:9]2[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2.S(=O)(=O)(O)O.C1(C)C=CC=CC=1>O>[CH2:1]=[C:2]1[CH:3]2[CH2:11][CH:7]3[CH2:6][CH:5]([CH2:10][CH:9]1[CH2:8]3)[CH2:4]2

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 1140Toluene2×HCID 1365452-Methyl-2-adamantanol

Product 1

HCID 1366842-MethylideneadamantaneYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

One liter flask equipped with a Dean-Stark condenser was charged-with 166.3 g (1.0 mol) of 2-methyl-2-adamantanol (supplied by Sigma-Aldrich Co.), 2.0 g (20 mmol) of sulfuric acid and 500 g of toluene. The content was heated to the solvent reflux temperature. While toluene and water produced through the reaction were collected as an azeotrope by the Dean-Stark condenser, the reaction mixture was refluxed for 2 hours. After completion of the reaction, the catalyst was removed by washing the reaction mixture with water and the obtained organic phase was concentrated to dryness to give 152.5 g of white solid 2-methyleneadamantane (purity: 99.0%, yield: 98.0%).

Workup

  1. customOne liter flask equipped with a Dean-Stark condenser
  2. temperatureThe content was heated to the solvent
  3. temperaturereflux temperature
  4. customwere collected as an azeotrope by the Dean-Stark condenser
  5. temperaturethe reaction mixture was refluxed for 2 hours
  6. customAfter completion of the reaction
  7. customthe catalyst was removed
  8. washby washing the reaction mixture with water
  9. concentrationthe obtained organic phase was concentrated to dryness

Sources & evidence

ORD record
ord-14294a07891042589f18ef8b5691167d
Source dataset
uspto-grants-2006_12
Patent number
US07148363B2

Linked notes

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