Ethanol → 2-Bornanecarboxylic acid

HRID 1198008Notes

Reaction equation

HRID 1198008 reaction equation
[OH2:1].[C:2]1([CH3:12])[CH:7]=[CH:6][C:5](S(O)(=O)=O)=[CH:4][CH:3]=1.[CH2:13]([OH:15])C.[CH:16]1[CH:21]=CC(CO[C@H]2C(OCC3C=CC=CC=3)[C@@H](OCC3C=CC=CC=3)[C@H](O)C(O)[C@H]2O)=C[CH:17]=1>[Pd].O>[C:2]12([CH3:12])[C:16]([CH3:21])([CH3:17])[CH:5]([CH2:6][CH2:7]1)[CH2:4][CH:3]2[C:13]([OH:15])=[O:1]

Participants

6

Reactant 3

HCID 702EthanolHCID 521998p-Toluenesulfonic acid monohydrateHCID 30355961,5,6-Tri-O-benzylmyoinositol

Product 1

HCID 5655942-Bornanecarboxylic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

The formed substance, 3,4-di-O-allyl-5,6-di-O-benzyl-myo-inositol (12.1 g) together with dibutylin oxide (4.0 g) and dry benzene (150 ml) was heated under reflux for 2 hours. After evaporation of benzene and addition of dry dimethyl formamide (60 ml) and benzyl bromide (5.5 ml) the solution was kept at 50° C. for 24 hours. The crude product was chromatographed on silica gel (250 g) and eluted with ether-light petroleum to give 9.5 g of 1,5,6-tri-O-benzyl-3,4-di-O-allyl-myo-inositol. A mixture of the obtained product, toluene-p-sulphonic acid monohydrate (0.9 g), ethanol (190 ml), water (10 ml) and palladium-on-charcoal (1 g, 10% from Fluka) was heated under reflux with stirring for 4 hours. The crude product was chromatographed on silica gel and elution with ether-light petroleum (4:1) gave a compound, identified with NMR to be 1,5,6-tri-O-benzyl-myo-inositol. The described substances are racemic mixtures. If desired the racemic mixture of the latter one could be separated into the enantiomeric forms by forming diastereomers with camphanic acid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. customThe crude product was chromatographed on silica gel and elution with ether-light petroleum (4:1)
  4. customgave a compound
  5. additionthe racemic mixture of the latter one
  6. customcould be separated into the enantiomeric forms

Sources & evidence

ORD record
ord-9cdec1d2cf8146ee973310751ebaf883
Source dataset
uspto-grants-1994_01
Patent number
US05278332

Reaction notes

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