p-Toluenesulfonic acid monohydrate → 4-(3,3-Dimethyl-1-methylene-butyl)-benzonitrile

HRID 911667Notes

Reaction equation

HRID 911667 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O[C:14]([C:21]1[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=1)([CH3:20])[CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17]>C1(C)C=CC=CC=1.CCOC(C)=O>[CH3:17][C:16]([CH3:19])([CH3:18])[CH2:15][C:14]([C:21]1[CH:22]=[CH:23][C:24]([C:25]#[N:26])=[CH:27][CH:28]=1)=[CH2:20]

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 576565864-(1-Hydroxy-1,3,3-trimethyl-butyl)-benzonitrile

Product 1

HCID 576562334-(3,3-Dimethyl-1-methylene-butyl)-benzonitrileYield 62%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Add p-toluenesulfonic acid monohydrate (308 mg, 1-62 mmol) to a solution of 4-(1-hydroxy-1,3,3-trimethyl-butyl)-benzonitrile (352 mg, 1.62 mmol) in toluene (10 mL). Heat the solution to 100° C. for 30 min. Cool the reaction mixture to room temperature, dilute the reaction mixture with EtOAc and wash the organic phase with saturated aqueous NaHCO3. Dry the organic phase over MgSO4, filter and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel eluting with hexane and hexane/EtOAc (98:2, 19:1) to give the desired intermediate as an oil (200 mg, 62%).

Workup

  1. temperatureCool the reaction mixture to room temperature
  2. washwash the organic phase with saturated aqueous NaHCO3
  3. dry with materialDry the organic phase over MgSO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. customPurify the crude mixture by chromatography on silica gel eluting with hexane and hexane/EtOAc (98:2, 19:1)

Sources & evidence

ORD record
ord-3f2a45bc45954688b79d88f3d1cfe997
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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