Sulfuric Acid → Chromic Acid

HRID 365161Notes

Reaction equation

HRID 365161 reaction equation
[O-2:1].[O-2:2].[O-2:3].[Cr+6:4].S(=O)(=O)(O)[OH:6].[CH:10]1([CH:16]([OH:19])[C:17]#[CH:18])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>O.CC(C)=O>[Cr:4]([OH:6])([OH:3])(=[O:2])=[O:1].[CH:10]1([C:16](=[O:19])[C:17]#[CH:18])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

7

Reactant 3

HCID 1118Sulfuric AcidHCID 199445alpha-EthynylcyclohexanemethanolHCID 10219390chromium (VI) trioxide

Product 2

HCID 24425Chromic AcidHCID 103517531-Cyclohexyl-2-propyn-1-one

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

A solution of chromic acid was prepared by dissolving 106.88 g chromium trioxide in 400 ml water and then adding 92 ml concentrated sulfuric acid. This solution is added in dropwise fashion over a 3 hr. period to an ice cooled, stirred solution of 120 g 3-cyclohexyl-1-propyn-3-ol in 175 ml acetone. The resulting mixture was diluted with 500 ml water and the product was extracted into 1 liter of diethyl ether. The ether extract was washed with 250 ml saturated sodium bisulfite solution and was dried over sodium sulfate. The diethyl ether was removed by distillation under nitrogen atmosphere and the resulting residue was purified by Kugelrohr distillation (65° C., 0.1 mm Hg) to give 84.9 g of 1-cyclohexyl-2-propyn-1-one as an oil: MS m/z=136 (M+) Caled. for C9H12O:C, 79.37; H, 8.88. Found:C, 79.24; H, 8.6.

Workup

  1. additionThis solution is added in dropwise fashion over a 3 hr
  2. extractionthe product was extracted into 1 liter of diethyl ether
  3. extractionThe ether extract
  4. washwas washed with 250 ml saturated sodium bisulfite solution
  5. dry with materialwas dried over sodium sulfate
  6. customThe diethyl ether was removed by distillation under nitrogen atmosphere
  7. distillationthe resulting residue was purified by Kugelrohr distillation (65° C., 0.1 mm Hg)

Sources & evidence

ORD record
ord-f1e0fbf5c1c04dd79aff18e5bd839532
Source dataset
uspto-grants-1986_08
Patent number
US04608388

Reaction notes

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