Sodium Hydroxide → HCID 15727606, compound

HRID 2080909Notes

Reaction equation

HRID 2080909 reaction equation
OC(C)(C)[C:3]#[C:4][C:5]1[CH:6]=[C:7]([CH:16]=[CH:17][CH:18]=1)[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:9].[OH-].[Na+]>C1(C)C=CC=CC=1>[C:4]([C:5]1[CH:6]=[C:7]([CH:16]=[CH:17][CH:18]=1)[C:8]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:9])#[CH:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67103471HCID 67103471, compound

Product 1

HCID 15727606HCID 15727606, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
120 °C

Procedure

In a 100 ml two-necked flask having a reflux condenser were charged 1.45 g (5.5 mmol) of 3-(3-hydroxy-3-methyl-1-butynyl)benzophenone and 230 mg (5.8 mmol) of NaOH (Kishida Chemical Co., Ltd.; 0.7 mm particles, 986) and air in the flask was replaced by Ar gas. 30 ml of toluene was added to the mixture and the mixture was heated at 120° C. under reflux 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 and the solvent was removed by distillation under reduced pressure using an evaporator. The resultant crude reaction product was purified by column chromatography (Hexane/AcOEt=30/1) using silica gel to obtain 0.9 g of 3-ethynylbenzophenone as orange solid. (Yield: 80%)

Workup

  1. customIn a 100 ml two-necked flask having
  2. temperatureunder reflux for 0.5 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=30/1)

Sources & evidence

ORD record
ord-1606ed34a0e04f3d8122d77d9e929551
Source dataset
uspto-grants-2011_04
Patent number
US07932398B2

Reaction notes

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