Hydrochloric Acid → 4-Hydroxy-4-(pyridin-2-yl)cyclohexanone

HRID 2225225Notes

Reaction equation

HRID 2225225 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1([OH:17])[CH2:16][CH2:15][C:10]2(OCC[O:11]2)[CH2:9][CH2:8]1.Cl.C(=O)(O)[O-].[Na+]>C1COCC1.O.C(OCC)C>[OH:17][C:7]1([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[CH2:8][CH2:9][C:10](=[O:11])[CH2:15][CH2:16]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 21187637HCID 21187637, compound

Product 1

HCID 211876304-Hydroxy-4-(pyridin-2-yl)cyclohexanoneYield 31%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

8-(2-Pyridinyl)-1,4-dioxaspiro[4.5]decan-8-ol (2.70 g) was dissolved in 1:1 THF/H2O (20 mL) then 3N HCl (10 mL) added. Refluxed for 2 hours then stirred overnight at room temperature. Worked up by slowly adding neat sodium bicarbonate until foaming ceased then extracted the mixture 3 times with ethyl acetate. The organic layers were combined, dried (sodium sulfate) and stripped to give an amber oil which solidified. The solids were dissolved in diethyl ether (10 mL). Hexanes (10 mL) were added which precipitated the solids which were then filtered to give 4-hydroxy-4-(pyridin-2-yl)cyclohexanone (680 mg) as a tan solid. MS found: (M+H)+=192.1.

Workup

  1. temperatureRefluxed for 2 hours
  2. extractionceased then extracted the mixture 3 times with ethyl acetate
  3. dry with materialdried (sodium sulfate)
  4. customto give an amber oil which
  5. customprecipitated the solids which
  6. filtrationwere then filtered

Sources & evidence

ORD record
ord-2373953906124985b991acae3a0b87c0
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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