Isopropanol → 4820-56-8

HRID 1580749Notes

Reaction equation

HRID 1580749 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]2[C:17]3[CH2:16][CH2:15][C@@:13]4([CH3:14])[C@@H:9]([CH2:10][CH2:11][C@@H:12]4[OH:21])[C:8]=3[CH:7]=[CH:6][C:5]=2[CH:4]=1.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.CC(O)C>CC(C)=O>[CH3:14][C:13]12[C:12](=[O:21])[CH2:11][CH2:10][CH:9]1[C:8]1[CH:7]=[CH:6][C:5]3[CH:4]=[C:3]([O:2][CH3:1])[CH:20]=[CH:19][C:18]=3[C:17]=1[CH2:16][CH2:15]2

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 12094734HCID 12094734, compoundHCID 131709961Jones' reagent

Product 1

HCID 3127874820-56-8

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

This crude alcohol was dissolved in 10 ml of acetone and the resulting solution was stirred and cooled in an ice bath while 0.5 ml of Jones reagent (CrO3 -H2SO4) was added dropwise. After stirring for 5 min. the excess oxidant was decomposed with 1 ml of 2-propanol. The resulting mixture was treated with ice water and most of the acetone was evaporated at reduced pressure. Extraction of the residual suspension with three portions of chloroform followed by washing the extracts with saturated NaHCO3 solution then drying (MgSO4), filtration and concentration at aspirator pressure gave 0.262g of partially crystalline, crude equilenin methyl ether. A combination of preparative thin layer chromatography (silica gel; benzene:ethyl acetate, 95:5) and recrystallization from methanol gave 0.0775g (27.6%) of colorless needles, m.p. 192°-194° which was essentially pure equilenin methyl ether. Another recrystallization from methanol gave colorless solid, m.p. 195°-196°, [α]D25 + 88.72°(c 0.86, dioxane).

Workup

  1. additionwas added dropwise
  2. stirringAfter stirring for 5 min. the excess oxidant
  3. customwas evaporated at reduced pressure
  4. extractionExtraction of the residual suspension with three portions of chloroform
  5. washby washing the extracts with saturated NaHCO3 solution
  6. customthen drying
  7. filtration(MgSO4), filtration and concentration at aspirator pressure

Sources & evidence

ORD record
ord-5c6b66697adf4829847d016d5b60d67d
Source dataset
uspto-grants-1976_01
Patent number
US03933870

Reaction notes

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