Acetone → HCID 15405233, compound

HRID 443193Notes

Reaction equation

HRID 443193 reaction equation
CC(C)=[O:3].S(=O)(=O)(O)O.[O:10]1[CH2:20][C:11]1([CH3:21])[CH:12]1[CH2:17][CH2:16][CH:15]([CH3:18])[CH2:14][CH:13]1[OH:19]>>[CH:15]1([CH3:18])[CH2:16][CH2:17][CH:12]([C:11]([OH:3])([CH3:21])[CH2:20][OH:10])[CH:13]([OH:19])[CH2:14]1

Participants

4

Reactant 3

HCID 180AcetoneHCID 1118Sulfuric AcidHCID 11457927HCID 11457927, compound

Product 1

HCID 15405233HCID 15405233, compound

Procedure

Into a solution of acetone (116 g; 2 mol) and a 3% aqueous solution of sulfuric acid (35 g) was added 8,9-epoxy-p-menthan-3-ol (17 g; 0.1 mol), and the mixture was stirred at room temperature for 16 hours. Then, the acetone was distilled and recovered, and the concentrated solution was mixed with water (40 ml) and heated to within 80° C. of the distilling temperature to completely recover the acetone. The remaining aqueous solution was cooled, neutralized with a 10% aqueous solution of sodium carbonate, and saturated with sodium chloride. The reaction product was extracted with THF, dried over anhydrous magnesium sulfate, and concentrated to give a crude product (19 g). The crude product was purified by column chromatography on silica gel. That is, the crude product was eluted with 50% ethyl acetate-n-hexane, then eluted with ethyl acetate only, and the eluate was concentrated to give a highly pure title compound (4) (7 g; a mixture of diastereomers). This was a mixture of solid and liquid, and the mixing ratio of diastereomers was calculated as 7:3 by measuring with NMR. Analytical results on the title compound are given below. Optical rotation [α]D25=+15.6 (c=1, EtOH)

Workup

  1. distillationThen, the acetone was distilled
  2. customrecovered
  3. additionthe concentrated solution was mixed with water (40 ml)
  4. temperatureheated to within 80° C. of the distilling temperature
  5. customto completely recover the acetone
  6. temperatureThe remaining aqueous solution was cooled
  7. extractionThe reaction product was extracted with THF
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated
  10. customto give a crude product (19 g)
  11. customThe crude product was purified by column chromatography on silica gel
  12. washthe crude product was eluted with 50% ethyl acetate-n-hexane
  13. washeluted with ethyl acetate only
  14. concentrationthe eluate was concentrated

Sources & evidence

ORD record
ord-7dcc1848141d49ddae0993abd6ba7a3c
Source dataset
uspto-grants-1999_04
Patent number
US05892133

Reaction notes

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