Sulfuric Acid → 3-Ethenyltricyclo[3.3.1.13,7]decan-1-ol

HRID 2302110Notes

Reaction equation

HRID 2302110 reaction equation
O[CH:2]([C:4]12[CH2:13][CH:8]3[CH2:9][CH:10]([CH2:12][C:6]([OH:14])([CH2:7]3)[CH2:5]1)[CH2:11]2)[CH3:3].S(=O)(=O)(O)O>C1(C=CC(O)=CC=1)O.C1(C)C=CC=CC=1>[CH:2]([C:4]12[CH2:13][CH:8]3[CH2:9][CH:10]([CH2:12][C:6]([OH:14])([CH2:7]3)[CH2:5]1)[CH2:11]2)=[CH2:3]

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 219334193-Hydroxy-α-methyltricyclo[3.3.1.13,7]decane-1-methanol

Product 1

HCID 144390653-Ethenyltricyclo[3.3.1.13,7]decan-1-olYield 55.1%

Reagents, catalysts & solvents 2

HCID 785HydroquinoneCatalystHCID 1140TolueneSolvent

Procedure

To 3 g of 3-(1-hydroxyethyl)-1-adamantanol were added 60 ml of toluene, 0.4 g of 98% sulfuric acid, and 0.01 g of hydroquinone, and the resultant mixture was stirred for 5 hours with azeotropic distillation and dehydration. The reaction mixture was cooled, was washed with a saturated aqueous sodium bicarbonate and saturated sodium chloride aqueous solution, and was then concentrated. The residue was purified by column chromatography on a silica gel (SiO2 80 g, developing solution: hexane/ethyl acetate=10/1) to give 1.5 g of 3-vinyl-1-adamantanol.

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwas washed with a saturated aqueous sodium bicarbonate and saturated sodium chloride aqueous solution
  3. concentrationwas then concentrated
  4. customThe residue was purified by column chromatography on a silica gel (SiO2 80 g, developing solution: hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-b3ae3d578fdd44319a2b420ad28ad2a9
Source dataset
uspto-grants-2002_08
Patent number
US06429314B1

Reaction notes

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