Water → Bicyclo[2.2.1]heptane-2,3-diol

HRID 1007625

Reaction equation

HRID 1007625 reaction equation
[O:1]1[CH:7]2[CH:2]1[CH:3]1[CH2:8][CH:6]2[CH2:5][CH2:4]1.O.S(=O)(=O)(O)[OH:11]>CC(C)=O>[OH:11][CH:2]1[CH:7]([OH:1])[CH:6]2[CH2:8][CH:3]1[CH2:4][CH2:5]2

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 18463exo-2,3-Epoxynorbornane

Product 1

HCID 85735Bicyclo[2.2.1]heptane-2,3-diol

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Into a four-neck flask (200 ml) were fed 20.3 g (185 mmol) of 2,3-epoxynorbornane, 50 ml of water, 25 ml of acetone, and 50 μl of sulfuric acid, and the reaction mixture was refluxed at 40° C. for 6 hours. After complete reaction, an object compound was extracted with each 40 ml of diethylether five times, and the resultant extract was washed with saturated salt solution (braine), and was dried with sodium sulfate to obtain 2,3-dihydroxynorbornane.

Workup

  1. customInto a four-neck flask (200 ml) were fed
  2. customAfter complete reaction
  3. extractionan object compound was extracted with each 40 ml of diethylether five times
  4. extractionthe resultant extract
  5. washwas washed with saturated salt solution (braine)
  6. dry with materialwas dried with sodium sulfate

Sources & evidence

ORD record
ord-5d2bc6da749c4c62bd5f9b33b471649e
Source dataset
uspto-grants-2004_09
Patent number
US06794528B2

Linked notes

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