3-Hexyne-2,5-diol → 5-Hydroxy-3-hexyn-2-one

HRID 260018Notes

Reaction equation

HRID 260018 reaction equation
[CH3:1][CH:2]([OH:8])[C:3]#[C:4][CH:5]([OH:7])[CH3:6].[OH:9][CH:10]([CH3:16])[C:11]#[C:12][C:13](=[O:15])[CH3:14]>S(=O)(=O)(O)O.O.CC(C)=O.[O-2].[O-2].[O-2].[Cr+6]>[CH3:1][C:2](=[O:8])[C:3]#[C:4][C:5](=[O:7])[CH3:6].[OH:15][CH:13]([CH3:14])[C:12]#[C:11][C:10](=[O:9])[CH3:16]

Participants

8

Reactant 2

HCID 181983-Hexyne-2,5-diolHCID 108986755-Hydroxy-3-hexyn-2-one

Product 2

HCID 108986755-Hydroxy-3-hexyn-2-oneHCID 114123563-Hexyne-2,5-dione

Reagents, catalysts & solvents 4

HCID 10219390chromium (VI) trioxideCatalystHCID 180AcetoneSolventHCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Procedure

To prepare Hex-3-yne-2,5-dioxe: Chromium trioxide (100 g) in concentrated sulphuric acid (90 ml) and water (550 ml) was added with vigorous stirring over 2 hours to hex-3-yne-2,5-diol (28 g) and 5-hydroxyhex-3-yn-2-one (28 g) in acetone (400 ml) at -5° to 0° C. After 1 hour, water (150 ml) was added and the solution extracted with ether. The extract was washed (aqueous NaHCO3), dried (MgSO4) and distilled to give crude hex-3-yne-2,5-dione (3-6 g), B.P. 50° (bath) at 0.15 m Hg ad 5-hydroxy-hex-3-yne-2-one (B.P. 50°-75° at 0.2 mm Hg) 23 g.

Workup

  1. extractionthe solution extracted with ether
  2. washThe extract was washed (aqueous NaHCO3)
  3. dry with materialdried (MgSO4)
  4. distillationdistilled

Sources & evidence

ORD record
ord-8887ed186da84e40922bb534bdc2e1fa
Source dataset
uspto-grants-1996_06
Patent number
US05525480

Reaction notes

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