HCID 12548507, compound → 4,4-Di(hydroxymethyl)bicyclo(2.2.1)heptene

HRID 67941

Reaction equation

HRID 67941 reaction equation
C([O:3][C:4]([C:6]1([C:13](OCC)=[O:14])[CH2:11][CH:10]2[CH2:12][CH:7]1[CH:8]=[CH:9]2)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[OH:3][CH2:4][C:6]1([CH2:13][OH:14])[CH2:11][CH:10]2[CH2:12][CH:7]1[CH:8]=[CH:9]2

Participants

4

Reactant 2

HCID 12548507HCID 12548507, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 1109174,4-Di(hydroxymethyl)bicyclo(2.2.1)hepteneYield 140.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Into a solution containing 2,2-bisethoxycarbonyl-5-norbornene (10 g) in dry tetrahydrofuran (100 ml) was added a mixture of lithium aluminum hydride (4.3 g) and dry tetrahydrofuran (100 ml) with stirring at room temperature. The reaction mixture was refluxed for 2 hours. After consumption of excess LiAlH4 by addition of water, the reaction mixture was concentrated to give a residue, which was extracted with chloroform. The extract was washed with a saturated NaCl solution, dried and concentrated to give as a solid substance 2,2-bishydroxymethyl-5-norbornene (Compound No. 21-1) (9.1 g), M.P., 108°-110° C. (recrystallization from isopropanol). IRνmaxNujol (cm-1): 3300, 2950, 1020.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was refluxed for 2 hours
  3. customAfter consumption of excess LiAlH4
  4. additionby addition of water
  5. concentrationthe reaction mixture was concentrated
  6. customto give a residue, which
  7. extractionwas extracted with chloroform
  8. washThe extract was washed with a saturated NaCl solution
  9. customdried
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-b474c9fa173143b3bd54aab6cb69a1fa
Source dataset
uspto-grants-1982_08
Patent number
US04347254

Linked notes

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