Sodium Hydroxide → 1-(4-Ethynylphenyl)ethan-1-one

HRID 1095234Notes

Reaction equation

HRID 1095234 reaction equation
C[C:2]1[C:3](C)=[C:4]([C:11]#[C:12]CO)[CH:5]=[CH:6][C:7]=1[C:8](=[O:10])[CH3:9].[OH-].[Na+]>C1(C)C=CC=CC=1>[C:8]([C:7]1[CH:6]=[CH:5][C:4]([C:11]#[CH:12])=[CH:3][CH:2]=1)(=[O:10])[CH3:9]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66784133Dimethylhydroxymethyl-4-acetylphenylacetylene

Product 1

HCID 51236261-(4-Ethynylphenyl)ethan-1-oneYield 56%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
120 °C

Procedure

1.45 g (7.17 mmol) of dimethylhydroxymethyl-4-acetylphenylacetylene and 301 mg (7.53 mmol) of NaOH (KISHIDA CHEMICAL CO., Ltd., 0.7 mm granular, 98%) were placed in a 100 mL two-neck flask equipped with a reflux condenser and the air inside the flask was replaced with Ar. 36 mL of toluene was added thereto and the mixture was refluxed at 120° C. for 15 minutes. 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. Then, 25 mL of hexane was added to the resulting crude reaction product and the mixture was cooled to give 4-acetylphenylethyne as a yellow solid. (0.74 g, yield: 56%).

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. additionThen, 25 mL of hexane was added to the resulting crude
  6. customreaction product
  7. temperaturethe mixture was cooled

Sources & evidence

ORD record
ord-51a39bf682344d698bde5af78593cdee
Source dataset
uspto-grants-2012_03
Patent number
US08137821B2

Reaction notes

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