Water → 3-Oxocyclohexane-1-carboxylic acid

HRID 1526497Notes

Reaction equation

HRID 1526497 reaction equation
S(=O)(=O)(O)O.O.[OH:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]([OH:16])=[O:15])[CH2:9]1.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[O:7]=[C:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]([OH:16])=[O:15])[CH2:9]1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 5255726Cyclohexanecarboxylic acid, 3-hydroxy-HCID 131709961Jones' reagent

Product 1

HCID 27602523-Oxocyclohexane-1-carboxylic acidYield 80.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The Jones oxidation reagent was prepared from sulfuric acid (30 mL), CrO3 (8.1 g) and H2O (30 mL) in an ice/water bath. A solution of 3-hydroxycyclohexane-1-carboxylic acid (11 g, 76.3 mmol, 1.00 equiv) in acetone (150 mL) was added slowly the prepared Jones reagent at 0° C. in 30 min. After addition, the resulting solution was stirred for 2 h at room temperature and the solids were filtered out. The resulting solution was extracted with DCM (3×100 mL). The combined organic layers were washed with brine and dried over sodium sulfate and concentrated under vacuum to give the desired 3-oxocyclohexane-1-carboxylic acid (8.7 g, crude) as a yellow oil.

Workup

  1. additionAfter addition
  2. filtrationthe solids were filtered out
  3. extractionThe resulting solution was extracted with DCM (3×100 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-0d347e9b74744624b5bd57bdca18ce4b
Source dataset
uspto-grants-2015_07
Patent number
US09085586B2

Reaction notes

Loading…