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

HRID 549937Notes

Reaction equation

HRID 549937 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>O1CCCC1>[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

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21187637HCID 21187637, compound

Product 1

HCID 211876304-Hydroxy-4-(pyridin-2-yl)cyclohexanoneYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

8-Pyridin-2-yl-1,4-dioxaspiro[4.5]decan-8-ol (1.44 g) was dissolved in tetrahydrofuran (25 ml). 2M hydrochloric acid (25 ml) was added and the solution stirred at room temperature overnight. The THF was removed in vacuo and remaining solution made basic with 2M aqueous sodium hydroxide and partitioned with dichloromethane (2×100 ml). Combined organics were dried (sodium sulphate) and concentrated in vacuo to give 4-hydroxy-4-pyridin-2-ylcyclohexanone as an off-white solid (1.07 g, 92%).

Workup

  1. customThe THF was removed in vacuo
  2. custompartitioned with dichloromethane (2×100 ml)
  3. dry with materialCombined organics were dried (sodium sulphate)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-00c0530ef2164911b874a2af9b83bfa2
Source dataset
uspto-grants-2011_05
Patent number
US07943768B2

Reaction notes

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