Toluene → HCID 86139837, compound

HRID 1095219Notes

Reaction equation

HRID 1095219 reaction equation
C[C:2]1[C:3](C)=[C:4]([C:15]#[C:16]CO)[C:5]2[CH2:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.[OH-].[Na+].C1(C)C=CC=CC=1>CCCCCC>[C:4]1([C:15]#[CH:16])[C:5]2[CH2:6][C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:13]=2[CH:14]=[CH:2][CH:3]=1

Participants

5

Reactant 3

HCID 1140Toluene2×HCID 14798Sodium HydroxideHCID 66784012HCID 66784012, compound

Product 1

HCID 86139837HCID 86139837, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
120 °C

Procedure

1.74 g (7 mmol) of Dimethylhydroxymethyl-2-fluorenylacetylene and 294 mg (7.35 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. 35 mL of toluene was added thereto and the mixture was refluxed at 120° C. for 1 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 distilled off under reduced pressure by an evaporator. The resulting crude reaction product was dissolved in 40 ml of hexane at 70° C. and then the insolubles were filtered off. The filtrate was cooled to give 2-fluorenylethyne, i.e., the desired compound as a yellow solid (1.12 g, yield: 84%).

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. distillationThe solvent was distilled off under reduced pressure by an evaporator
  5. customThe resulting crude reaction product
  6. filtrationthe insolubles were filtered off
  7. temperatureThe filtrate was cooled

Sources & evidence

ORD record
ord-10151211b5dd499fa2da2838e9ee9a70
Source dataset
uspto-grants-2012_03
Patent number
US08137821B2

Reaction notes

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