Acetone → HCID 86734702, compound

HRID 1679309Notes

Reaction equation

HRID 1679309 reaction equation
Cl[CH:2]([C:6](=[O:8])[CH3:7])[CH2:3][CH2:4]O.[S:9]1C=CC=C1CC([O-])=O.[K+].[CH3:19][C:20](C)=[O:21]>>[C:20]([O:21][C:2]1[CH2:3][CH2:4][O:8][C:6]=1[CH3:7])(=[S:9])[CH3:19]

Participants

4

Reactant 3

HCID 180AcetoneHCID 40868603-chloro-5-hydroxypentan-2-oneHCID 23696799Potassium 2-thienylacetate

Product 1

HCID 86734702HCID 86734702, compound

Procedure

13.65 g (0.1 m) of 3-chloro-3-acetylpropanol (b.p. 90°-110° C/2mmHg; nD20 1.4740) prepared according to the method described by J. R. Stevens and G. A. Stein, J.Am.Chem.Soc. 62, 1045 (1940), were refluxed with 18.6 g (0.15 m) potassium thiolacetate in 100 ml of acetone for about 2 hours. After cooling the reaction mixture was filtered and the filtrate evaporated to dryness and the residue dissolved in water. The aqueous solution was extracted five times with chloroform and the combined extracts washed, dried and evaporated. Distillation of the residue yielded 3-thioacetoxy-2-methyl-4,5-dihydrofuran, b.p. 57°-59° C/0.6 mmHg.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. filtrationwas filtered
  3. customthe filtrate evaporated to dryness
  4. dissolutionthe residue dissolved in water
  5. extractionThe aqueous solution was extracted five times with chloroform
  6. washthe combined extracts washed
  7. customdried
  8. customevaporated
  9. distillationDistillation of the residue

Sources & evidence

ORD record
ord-7522f607f97649d0920b401093af52b3
Source dataset
uspto-grants-1978_03
Patent number
US04080367

Reaction notes

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