Sodium Hydroxide → HCID 86690525, compound

HRID 241497Notes

Reaction equation

HRID 241497 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[C:23]([C:27]1[CH:32]=[CH:31][C:30]([C:33]#[C:34][CH:35]([OH:48])[C:36]#[C:37][C:38]2[CH:43]=[CH:42][C:41]([C:44]([CH3:47])([CH3:46])[CH3:45])=[CH:40][CH:39]=2)=[CH:29][CH:28]=1)([CH3:26])([CH3:25])[CH3:24].[OH-].[Na+]>CC(C)=O.O>[C:44]([C:41]1[CH:42]=[CH:43][C:38]([C:37]#[C:36][C:35](=[O:48])[C:34]#[C:33][C:30]2[CH:29]=[CH:28][C:27]([C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:32][CH:31]=2)=[CH:39][CH:40]=1)([CH3:47])([CH3:46])[CH3:45]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 86690523HCID 86690523, compound2×

Product 1

HCID 86690525HCID 86690525, compoundYield 82.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

In a nitrogen atmosphere, while a solution obtained by dissolving 27.5 g of Dess-Martin periodinane in 170 ml of (ultra-dehydrated) acetone is being cooled with ice water, a solution obtained by dissolving 19.5 g of (B) 1,5-bis(4-tert-butylphenyl)-penta-1,4-diyn-3-ol in 70 ml of (ultra-dehydrated) acetone is added to the above solution, followed by stirring at room temperature (23° C. to 25° C.) for 3 hours. A solution obtained by dissolving 5 g of sodium hydroxide in 25 ml of water is added to the reaction mixture, and the yellow precipitate is removed by suction filtration, and washed with acetone. The acetone filtrate is concentrated by distillation under reduced pressure, and 300 ml of ethyl acetate is poured into the obtained concentrated liquid to extract the organic substances, and the separated organic layer is washed with water. The concentrated organic layer is purified by being recrystallized sequentially from a mixed solvent of acetone and hexane and then from a mixed solvent of acetone and ethanol, thereby obtaining 16.0 g of (C) 1,5-bis(4-tert-butylphenyl)-penta-1,4-diyn-3-one. The yield of this stage is 82.5%.

Workup

  1. customIn a nitrogen atmosphere, while a solution obtained
  2. customa solution obtained
  3. additionis added to the above solution
  4. customA solution obtained
  5. additionis added to the reaction mixture
  6. customthe yellow precipitate is removed by suction filtration
  7. washwashed with acetone
  8. concentrationThe acetone filtrate is concentrated by distillation under reduced pressure, and 300 ml of ethyl acetate
  9. additionis poured into the obtained
  10. concentrationconcentrated liquid
  11. extractionto extract the organic substances
  12. washthe separated organic layer is washed with water
  13. customThe concentrated organic layer is purified
  14. customby being recrystallized sequentially from a mixed solvent of acetone and hexane

Sources & evidence

ORD record
ord-fbff8afd9a874ad6a887d927413c3c74
Source dataset
uspto-grants-2014_02
Patent number
US08652718B2

Reaction notes

Loading…