Sulfuric Acid → 2,2,7,7-Tetramethylcycloheptan-1-ol

HRID 1249329Notes

Reaction equation

HRID 1249329 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)C.[CH3:12][C:13]1([CH3:23])[CH2:19][CH2:18][CH2:17][CH2:16][C:15]([CH3:21])([CH3:20])[C:14]1=[O:22].S(=O)(=O)(O)O>O>[CH3:12][C:13]1([CH3:23])[CH2:19][CH2:18][CH2:17][CH2:16][C:15]([CH3:21])([CH3:20])[CH:14]1[OH:22]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 3283Diethyl Ether2×HCID 132121452,2,7,7-Tetramethylcycloheptan-1-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 137825582,2,7,7-Tetramethylcycloheptan-1-olYield 98.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Lithium aluminium hydride (3.80 g, 0.1 mole) and dried diethyl ether (100 ml) were added to a one liter four-necked flask equipped with a mechanical stirrer, a dropping funnel, a thermometer, a reflux condenser and a calcium chloride tube and stirred at room temperature. A mixed solution of 2,2,7,7-tetramethylcycloheptanone (33.66 g, 0.2 moles)/dried diethyl ether (60 ml) was dropped into the mixture in 1 hour while stirring at room temperature. The mixture was stirred at room temperature for 1 hour. Subsequently, water (40 ml) and a 10% sulfuric acid aqueous solution (250 ml) were added in this order to the resulting reaction mixture to separate it into two layers. The resulting organic layer was washed twice with saturated saline solution (100 ml). The organic layer was dried over anhydrous magnesium sulfate and separated by filtration, followed by concentration and fractionation to obtain 33.45 g (yield 98.2%) of the captioned compound. This compound was a white solid having a woody, earthy, camphoraceous and hay-like odor.

Workup

  1. customequipped with a mechanical stirrer, a dropping funnel
  2. stirringwhile stirring at room temperature
  3. stirringThe mixture was stirred at room temperature for 1 hour
  4. customto separate it into two layers
  5. washThe resulting organic layer was washed twice with saturated saline solution (100 ml)
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. customseparated by filtration
  8. concentrationfollowed by concentration and fractionation

Sources & evidence

ORD record
ord-432b3dcaa45a4dd7aa3b7996fd86ddf4
Source dataset
uspto-grants-1986_12
Patent number
US04631147

Reaction notes

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