Sodium Hydroxide → 4-Benzoylphenylethyne

HRID 1095232

Reaction equation

HRID 1095232 reaction equation
C[C:2]1[C:3](C)=[C:4]([C:16]#[C:17]CO)[CH:5]=[CH:6][C:7]=1[C:8](=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[C:8]([C:7]1[CH:2]=[CH:3][C:4]([C:16]#[CH:17])=[CH:5][CH:6]=1)(=[O:15])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66784736HCID 66784736, compound

Product 1

HCID 121320044-BenzoylphenylethyneYield 76.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
120 °C

Procedure

1.85 g (7 mmol) of dimethylhydroxymethyl-4-benzoylphenylacetylene and 294 mg (7.35 mmol) of NaOH (KISHIDA CHEMICAL CO., Ltd., 0.7 mm granular, 98%) were placed in a 50 mL two-neck flask equipped with a reflux condenser and the air inside the flask was replaced with Ar. 35 mL of toluene was added thereto and the mixture was refluxed at 120° C. for 0.5 hour. Toluene was added to the reaction mixture and the mixture was washed with a saturated aqueous ammonium chloride solution and dried over magnesium sulfate, followed by distilling off of the solvent under reduced pressure by an evaporator. The crude reaction product was purified by column chromatography (Hexane/AcOEt=10/1) using silica gel to give 4-benzoylphenylethyne as a pale brown solid (1.1 g, yield: 76%).

Workup

  1. customequipped with a reflux condenser
  2. washthe mixture was washed with a saturated aqueous ammonium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. distillationby distilling off of the solvent under reduced pressure by an evaporator
  5. customThe crude reaction product
  6. customwas purified by column chromatography (Hexane/AcOEt=10/1)

Sources & evidence

ORD record
ord-4e35b02948d74e6db79e2694cfbf7142
Source dataset
uspto-grants-2012_03
Patent number
US08137821B2

Linked notes

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