Carbonic Acid → 2-Hydroxy-2,4-dimethyl-3-pentanone

HRID 1262981Notes

Reaction equation

HRID 1262981 reaction equation
[CH3:1][CH:2]([C:4](=[O:8])[CH:5]([CH3:7])[CH3:6])[CH3:3].BrBr.[OH:11]C(O)=O>C(Cl)(Cl)Cl>[OH:11][C:2]([CH3:3])([C:4](=[O:8])[CH:5]([CH3:7])[CH3:6])[CH3:1]

Participants

5

Procedure

To a stirred solution of 28.3 ml. (0.2 mole) 2,4-dimethyl-3-pentanone in 100 ml. chloroform was added dropwise 10.3 ml. (0.2 mole) bromine in 30 ml. of the same solvent. The resulting mixture was stirred for a few minutes, the solvent evaporated in vacuo, the residue taken up in 100 ml. ethanol. Water, 50 ml., and 10 M sodium hydroxide, 50 ml., added. The resulting mixture was stirred at reflux for one hour, diluted with 200 ml. water and extracted with 3×50 ml. ethyl ether. The extracts were dried (MgSO4) evaporated to dryness and the residue distilled to obtain 15.95 g. (61%) of the hydroxy-ketone, b.p. 60°-62° C./18 mm.

Workup

  1. customthe solvent evaporated in vacuo
  2. addition, added
  3. stirringThe resulting mixture was stirred
  4. temperatureat reflux for one hour
  5. additiondiluted with 200 ml
  6. extractionwater and extracted with 3×50 ml
  7. dry with materialThe extracts were dried (MgSO4)
  8. customevaporated to dryness
  9. distillationthe residue distilled
  10. customto obtain 15.95 g

Sources & evidence

ORD record
ord-6b485967578a48ac9bd7e88310a992f5
Source dataset
uspto-grants-1984_06
Patent number
US04454328

Reaction notes

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