Hydrochloric Acid → 3-Ethynylbenzonitrile

HRID 606787

Reaction equation

HRID 606787 reaction equation
C(=O)([O-])[O-].[K+].[K+].C[Si]([C:11]#[C:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[C:16]#[N:17])(C)C.Cl>CO>[C:12]([C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[C:16]#[N:17])#[CH:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 225703183-[(Trimethylsilyl)ethynyl]benzonitrile

Product 1

HCID 120889643-EthynylbenzonitrileYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add potassium carbonate (0.138 g, 1 mmol) to a solution of 3-trimethylsilanylethynylbenzonitrile from PREPARATION 5 (2.0 g, 10.1 mmol) in methanol (50 mL). Stir the mixture at room temperature for 20 min and add a 10% aqueous hydrochloric acid solution (4 mL). Concentrate to a reduced volume, add diethyl ether and water and separate the phases. Wash once the aqueous phase with diethyl ether. Combine the organic phases, dry over sodium sulfate and concentrate to obtain the title compound as a solid (1.17 g, 92%).

Workup

  1. concentrationConcentrate to a reduced volume
  2. additionadd diethyl ether and water
  3. customseparate the phases
  4. washWash once the aqueous phase with diethyl ether
  5. dry with materialdry over sodium sulfate
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-0eabd544b1254993971a164e6b861429
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Linked notes

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