Dimethyl Sulfoxide → Ethyl 2-(3-oxocyclohexyl)acetate

HRID 1526488Notes

Reaction equation

HRID 1526488 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][CH:4]([CH:8](C(OCC)=O)[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:3]1.[Cl-].[Na+].CS(C)=O>O>[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][CH:4]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:3]1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 5234Sodium ChlorideHCID 3170491,3-Diethyl 2-(3-oxocyclohexyl)propanedioate

Product 1

HCID 11355886Ethyl 2-(3-oxocyclohexyl)acetateYield 110.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
180 °C

Procedure

A solution of 1,3-diethyl 2-(3-oxocyclohexyl)propanedioate (28.50 g, 111.20 mmol, 1.00 equiv) and sodium chloride (7.02 g, 1.10 equiv) in a mixture of water (4 mL)/DMSO (80 mL) was heated for 24 h at 180° C. in an oil bath. After cooled down to r.t, the reaction was then diluted with water, extracted with 3×300 mL of ethyl acetate. The organic layers were combined, washed with water and brine, dried over anhydrous sodium sulfate and concentrated under vacuum to give ethyl 2-(3-oxocyclohexyl)acetate (22.7 g, crude) as yellow oil which was used for next step without purification.

Workup

  1. temperatureAfter cooled down
  2. extractionextracted with 3×300 mL of ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-3fcd02889b0048589ba3d482638b605e
Source dataset
uspto-grants-2015_07
Patent number
US09085586B2

Reaction notes

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