Cyclohexanone → HCID 15473347, compound

HRID 2059716Notes

Reaction equation

HRID 2059716 reaction equation
[C:1]1(=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:8]1(=[O:15])[CH2:13][CH2:12][CH2:11][C:10](=[O:14])[CH2:9]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1>[C:8]1(=[O:15])[C:9]2[CH:2]3[CH2:3][CH2:4][CH2:5][CH2:6][CH:1]3[O:14][C:10]=2[CH2:11][CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 7967CyclohexanoneHCID 104341,3-CyclohexanedioneHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 15473347HCID 15473347, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of cyclohexanone (5.28 mL, 50.9 mmol), cyclohexane-1,3-dione (5.89 g, 50.9 mmol), and p-toluenesulfonic acid monohydrate (0.485 g, 2.55 mmol) in xylene (600 mL) was heated at reflux under a Dean Stark trap for 16 hours. The mixture was filtered and concentrated under reduced pressure. The residue was chromatographed on silica gel eluting with 0-30% ethyl acetate in hexanes to provide the title compound: 1H NMR (CDCl3) δ 1.21-1.31 (m, 2H), 1.43-1.57 (m, 3H), 1.72-1.83 (m, 1H), 1.96-2.08 (m, 4H), 2.33 (t, 2H), 2.41 (t, 2H), 2.96-3.06 (m, 1H), 4.61-4.69 (m, 1H); MS (DCl/NH3) m/z 193 (M+H)30.

Workup

  1. temperatureat reflux under a Dean Stark trap for 16 hours
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was chromatographed on silica gel eluting with 0-30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-47ea9f504df84296845ac6e31bc40c2d
Source dataset
uspto-grants-2012_10
Patent number
US08278311B2

Reaction notes

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