Acetone → 1,8-Cineole

HRID 1248037

Reaction equation

HRID 1248037 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)O.[CH3:9][CH2:10][CH2:11]CCCC.[CH3:16]C(C)=O>>[CH3:9][C:10]1([CH3:11])[O:6][C:5]2([CH3:16])[CH2:7][CH2:8][CH:1]1[CH2:3][CH2:4]2

Participants

4

Reactant 3

HCID 180AcetoneHCID 785Hydroquinone2×HCID 8900Heptane2×

Product 1

HCID 27581,8-Cineole

Procedure

Crystalline anhydrous hydroquinone (19.5 g) was added to a 1 cm diameter jacketed glass chromatography column filled with heptane. The heptane was then drained to the level of the top of the packed hydroquinone, cold acetone poured into the jacket to chill the column contents below -10° C., and Unitene-D (20 g) added. The column contents were then eluted with heptane (about 250 ml) with continued chilling over 2 hours. This removed most of the undesirable components of the feed. The jacket was then drained of coolant and the column warmed to room temperature. Continued elution with heptane provided a solution of 1.8-cineole (1.8 g) of 92.8% purity (solvent-free basis). This represents a 50% yield of 1,8-cineole present in the feedstock mixture.

Workup

  1. additionpoured into the jacket
  2. temperatureto chill the column contents below -10° C., and Unitene-D (20 g)
  3. additionadded
  4. washThe column contents were then eluted with heptane (about 250 ml)
  5. temperaturewith continued chilling over 2 hours
  6. customThis removed most of the undesirable components of the feed
  7. washContinued elution with heptane

Sources & evidence

ORD record
ord-1b1baecfde7746a2bb02cec0ef27caa0
Source dataset
uspto-grants-1985_06
Patent number
US04521608

Linked notes

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