Toluene → 1,4-Dioxaspiro[4.5]decane-8-carbonitrile, 8-(4-fluorophenyl)-

HRID 45186

Reaction equation

HRID 45186 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:15]#[N:16])[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=[O:24])=CC=1.[C:28]1([CH3:34])C=CC=CC=1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:15]#[N:16])[CH2:9][CH2:10][C:11]3([O:24][CH2:28][CH2:34][O:14]3)[CH2:12][CH2:13]2)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 918051-(4-Fluorophenyl)-4-oxocyclohexanecarbonitrile

Product 1

HCID 122302421,4-Dioxaspiro[4.5]decane-8-carbonitrile, 8-(4-fluorophenyl)-

Procedure

15 g of 1-(4-Fluoro-phenyl)-4-oxo-cyclohexanecarbonitrile (12) were dissolved in 500 mL of toluene, then 900 mg of p-toluene sulfonic acid were added and the reaction mixture was heated in a Dean-Stark apparatus for 6 h. The mixture was allowed to cool to room temperature and washed twice with saturated aqueous sodium bicarbonate solution and brine, dried over magnesium sulphate and evaporated to dryness to yield 17.9 g of the desired product. Rt=1.47 min (Method 5). Detected mass: 262.2 (M+H+).

Workup

  1. temperaturethe reaction mixture was heated in a Dean-Stark apparatus for 6 h
  2. washwashed twice with saturated aqueous sodium bicarbonate solution and brine
  3. dry with materialdried over magnesium sulphate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-eb57cc6faa9a46448c8693c8bd34b229
Source dataset
uspto-grants-2013_09
Patent number
US08541449B2

Linked notes

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