Sulfuric Acid → HCID 12702707, compound

HRID 971840Notes

Reaction equation

HRID 971840 reaction equation
[CH3:1][Si:2]([CH3:9])([CH3:8])/[CH:3]=[CH:4]\[CH:5]([OH:7])[CH3:6].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.[Cr](O)(O)(=O)=O.S(=O)(=O)(O)O>O.CC(C)=O>[CH3:1][Si:2]([CH3:9])([CH3:8])/[CH:3]=[CH:4]/[C:5](=[O:7])[CH3:6]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 24425Chromic AcidHCID 10419313HCID 10419313, compoundHCID 131709961Jones' reagent

Product 1

HCID 12702707HCID 12702707, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of 174.6 parts by weight of cis-4-(trimethylsilyl)-3-buten-2-ol (III) in 2000 parts by volume of acetone is chilled to -10° C. and treated slowly with an excess (350 parts by volume) of Jones Reagent (a solution of chromic acid and sulfuric acid in water) while keeping the internal temperature below 10° C. The resulting precipitate is allowed to settle and the supernatant is decanted and concentrated on a rotary evaporator at 25° C. to remove much of the acetone. The precipitate is dissolved in water and the solution is extracted with ethyl ether. The ether extract is added to the acetone residue and the combined solutions are washed with water, then with 5% aqueous hydrochloric acid, and again with water. The ether extract is then dried over sodium sulfate and the ether removed by vacuum distillation. The residue is taken up in 500 parts by volume of isopropanol and 20 parts by volume of concentrated aqueous hydrochloric acid is added. The mixture is stored at room temperature for 18 hours then diluted with 1000 parts by volume of benzene and washed repeatedly with water. The washes are extracted with 500 parts by volume of benzene and dried over sodium sulfate to yield trans-4-(trimethylsilyl)-3-buten-2-one (IV) which has a boiling point of 165°-169° C. and is represented by the following structural formula ##STR10##

Workup

  1. customthe internal temperature below 10° C
  2. customthe supernatant is decanted
  3. concentrationconcentrated on a rotary evaporator at 25° C.
  4. customto remove much of the acetone
  5. dissolutionThe precipitate is dissolved in water
  6. extractionthe solution is extracted with ethyl ether
  7. extractionThe ether extract
  8. additionis added to the acetone residue
  9. washthe combined solutions are washed with water
  10. extractionThe ether extract
  11. dry with materialis then dried over sodium sulfate
  12. customthe ether removed by vacuum distillation
  13. additionis added
  14. additionthen diluted with 1000 parts by volume of benzene
  15. washwashed repeatedly with water
  16. extractionThe washes are extracted with 500 parts by volume of benzene
  17. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-96048d4d76c1464189f4ab5dadf400ff
Source dataset
uspto-grants-1979_07
Patent number
US04161480

Reaction notes

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