Water → 6-Camphenol

HRID 1980459Notes

Reaction equation

HRID 1980459 reaction equation
[CH3:1][C:2]1([CH3:12])[C:7]([CH3:9])(O)[CH:6]2[CH2:10][CH:3]1[CH2:4][CH:5]2[OH:11].S(Cl)(Cl)=O.O>N1C=CC=CC=1>[CH3:1][C:2]1([CH3:12])[C:7](=[CH2:9])[C@H:6]2[C@H:5]([OH:11])[CH2:4][C@@H:3]1[CH2:10]2

Participants

5

Reactant 3

HCID 962WaterHCID 24386Thionyl ChlorideHCID 13493472HCID 13493472, compound

Product 1

HCID 1805376-CamphenolYield 6.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 5.0 ml of pyridine was dissolved 1.7 g of 2,2,3-trimethylbicyclo[2.2.1]heptan-3,5-diol and, then, 1.2 g of thionyl chloride was added dropwise to the solution at a temperature of -5° C. to 0° C. The mixture was stirred for 2 hours, after which it was poured into water and extracted with n-hexane. The extract was washed with dilute hydrochloric acid and an aqueous solution of sodium hydrogen carbonate in that order, dried over anhydrous magnesium sulfate, and distilled to remove the hexane. The residue was subjected to silica gel column chromatography to give 0.10 g of nojigiku alcohol. The physical properties of this product were in agreement with those of the nojigiku alcohol obtained in Example 1.

Workup

  1. extractionextracted with n-hexane
  2. washThe extract was washed with dilute hydrochloric acid
  3. dry with materialan aqueous solution of sodium hydrogen carbonate in that order, dried over anhydrous magnesium sulfate
  4. distillationdistilled
  5. customto remove the hexane

Sources & evidence

ORD record
ord-abc7af828dec49a28d8e545b199944fa
Source dataset
uspto-grants-1985_04
Patent number
US04510025

Reaction notes

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