4,4-Di(hydroxymethyl)bicyclo(2.2.1)heptene → Bicyclo(2.2.1)heptane-2,2-dimethanol

HRID 2276620Notes

Reaction equation

HRID 2276620 reaction equation
[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][C:2]2([CH2:10][OH:11])[CH2:8][OH:9].[H][H]>C(O)C.[Pd]>[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][C:2]2([CH2:8][OH:9])[CH2:10][OH:11]

Participants

5

Reactant 2

HCID 1109174,4-Di(hydroxymethyl)bicyclo(2.2.1)hepteneHCID 178418361HCID 178418361, compound

Product 1

HCID 85846Bicyclo(2.2.1)heptane-2,2-dimethanolYield 92.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

138.18 g of 5-norbornene-2,2-dimethanol (commercially available from Tokyo Kasei Industry Co., Ltd.) was dissolved in 481.63 g of ethanol, and 6.92 g of 5% Pd—C was added, then a hydrogen balloon was attached and the mixture was stirred for 6 hours. The Pd—C was filtered off, then the reaction solution was concentrated and dried to thereby obtain 129.83 g of 2,2-norbornanedimethanol (purity by gas chromatography: 99.1%, yield: 92.9%).

Workup

  1. filtrationThe Pd—C was filtered off
  2. concentrationthe reaction solution was concentrated
  3. customdried

Sources & evidence

ORD record
ord-f26d92e1904249fd96f58acec57d0281
Source dataset
uspto-grants-2015_09
Patent number
US09133090B2

Reaction notes

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