Sodium Hydroxide → HCID 11252737, compound

HRID 2080923Notes

Reaction equation

HRID 2080923 reaction equation
C[C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9]CO)=[C:4]([C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:3]=1C.[OH-].[Na+]>C1(C)C=CC=CC=1>[C:8]([C:5]1[CH:6]=[CH:7][CH:2]=[CH:3][C:4]=1[C:12]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:19])#[CH:9]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67103525HCID 67103525, compound

Product 1

HCID 11252737HCID 11252737, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
120 °C

Procedure

In a 100 ml two-necked flask having a reflux condenser were charged 2.6 g (9.9 mmol) of dimethylhydroxymethyl-2-benzoylphenylacetylene and 416 mg (10.4 mmol) of NaOH (Kishida Chemical Co., Ltd.; 0.7 mm particles, 98%) and air in the flask was replaced by Ar gas. 50 ml of toluene was added to the mixture and the mixture was heated at 120° C. under reflux for 0.25 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. The solvent was removed by distillation under reduced pressure using an evaporator. The resultant crude reaction product was purified by column chromatography (Hexane/AcOEt=20/1) using silica gel to obtain 1.7 g of 2-ethynylbenzophenone as orange solid. (Yield: 82%)

Workup

  1. customIn a 100 ml two-necked flask having
  2. temperatureunder reflux for 0.25 hour
  3. washthe mixture was washed with a saturated aqueous ammonium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed by distillation under reduced pressure
  6. customan evaporator
  7. customThe resultant crude reaction product
  8. customwas purified by column chromatography (Hexane/AcOEt=20/1)

Sources & evidence

ORD record
ord-532d73faccb44f2da3f16f4617ad85a1
Source dataset
uspto-grants-2011_04
Patent number
US07932398B2

Reaction notes

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