Water → HCID 59164563, compound

HRID 1441523Notes

Reaction equation

HRID 1441523 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1([S:19]([N:22]2[CH2:27][CH2:26][CH:25]([F:28])[CH2:24][CH2:23]2)(=[O:21])=[O:20])[CH2:18][CH2:17][C:12]2(OCC[O:13]2)[CH2:11][CH2:10]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C(O)(=O)C.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1([S:19]([N:22]2[CH2:27][CH2:26][CH:25]([F:28])[CH2:24][CH2:23]2)(=[O:20])=[O:21])[CH2:18][CH2:17][C:12](=[O:13])[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 59164565HCID 59164565, compound

Product 1

HCID 59164563HCID 59164563, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 21899381Acetic acid--water (1/1)Solvent

Procedure

The product of Step 2 (2.99 g, 7.14 mmol) and p-toluenesulfonic acid (1.62 g, 8.56 mmol) in acetic acid/water (40 ml/10 ml) were heated at 50° C. for 3 hours and then diluted (water) and extracted (diethyl ether). The organic phase was washed (saturated sodium hydrogen carbonate, brine), dried (magnesium sulfate) and evaporated in vacuo. The crude product was azeotroped with toluene, followed by ethyl acetate, followed by dichloromethane. The crude product then was chromatographed on silica, eluting with 30% ethyl acetate/isohexane to give the cyclohexanone (1.7 g, 64%).

Workup

  1. extractionextracted (diethyl ether)
  2. washThe organic phase was washed (saturated sodium hydrogen carbonate, brine)
  3. dry with materialdried (magnesium sulfate)
  4. customevaporated in vacuo
  5. customThe crude product was azeotroped with toluene
  6. customThe crude product then was chromatographed on silica
  7. washeluting with 30% ethyl acetate/isohexane

Sources & evidence

ORD record
ord-4716f0bd851e423abefe88c6493fe174
Source dataset
uspto-grants-2010_02
Patent number
US07655675B2

Reaction notes

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