Sulfuric Acid → HCID 86650280, compound

HRID 1889219Notes

Reaction equation

HRID 1889219 reaction equation
[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][S:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:22])=[O:21].[S:29](=[O:33])(=[O:32])([OH:31])[OH:30]>CC(C)=O.[O-2].[O-2].[O-2].[Cr+6]>[S:29](=[O:31])(=[O:30])([OH:33])[OH:32].[C:23]1([S:20]([O:19][CH2:18][CH2:17][O:16][CH2:15][CH2:14][O:13][CH2:12][CH2:11][O:10][CH2:9][CH2:8][O:7][CH2:6][CH2:5][O:4][CH2:3][C:2]([OH:30])=[O:1])(=[O:22])=[O:21])[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 2

HCID 1118Sulfuric AcidHCID 86650279HCID 86650279, compound

Product 2

HCID 1118Sulfuric AcidHCID 86650280HCID 86650280, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 180AcetoneSolvent

Procedure

A 1.5.M aqueous solution of sulfuric acid (10 mL) was prepared at 0° C. and stirred while chromium trioxide was added to give an orange solution. The alcohol 12 (1 g, 2.29 mmol) was dissolved in acetone (15 mL) and the solution added dropwise to the sulfuric acid at 0° C. The mixture was allowed to warm to rt and stirred for 16 h. The resulting green solution was filtered through celite and concentrated in vacuo. The resulting aqueous residue was diluted with H2O and extracted with CH2Cl2 (3×50 mL). The organic phase was dried over MgSO4 and concentrated in vacuo to give 13 (672 mg, 65%) as a pale yellow oil which was not purified further.

Workup

  1. additionwas added
  2. customto give an orange solution
  3. filtrationThe resulting green solution was filtered through celite and
  4. concentrationconcentrated in vacuo
  5. additionThe resulting aqueous residue was diluted with H2O
  6. extractionextracted with CH2Cl2 (3×50 mL)
  7. dry with materialThe organic phase was dried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-de5ac88c6d444dc0a3c848a20c050a05
Source dataset
uspto-grants-2013_08
Patent number
US08501991B2

Reaction notes

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