Pinacolone → HCID 200646, compound

HRID 1899875Notes

Reaction equation

HRID 1899875 reaction equation
[CH3:1][C:2](=[O:7])[C:3]([CH3:6])([CH3:5])[CH3:4].[CH:8]1[C:13]([CH:14]=O)=[CH:12][C:11]2[O:16][CH2:17][O:18][C:10]=2[CH:9]=1.[OH-].[Na+]>C(O)C.O>[O:18]1[C:10]2[CH:9]=[CH:8][C:13]([CH:14]=[CH:1][C:2](=[O:7])[C:3]([CH3:6])([CH3:5])[CH3:4])=[CH:12][C:11]=2[O:16][CH2:17]1

Participants

6

Reactant 3

HCID 6416PinacoloneHCID 8438PiperonalHCID 14798Sodium Hydroxide

Product 1

HCID 200646HCID 200646, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a mixture of pinacolone (55 g) and piperonal (75 g) in ethanol (200 ml) was added a sodium hydroxide (5.0 g) in water (115 ml) solution. The mixture solidified after stirring at room temperature for 2 days. Filtration collected 137 g of solid which was then dissolved in ethyl acetate (500 ml), washed with water (500 ml), and dried over anhydrous magnesium sulfate. Concentration and trituration in hexane yielded 104.5 g of colorless solid product, mp 94°-96° C. Using essentially the same procedures, additional alpha, beta-unsaturated ketones were prepared as intermediates and are listed in Table 5. [see Pace, E, Atti Acad Lincei, [6], 9, 778 (1929); Chemical Abstracts, 23, 4942, 1929].

Workup

  1. filtrationFiltration
  2. customcollected 137 g of solid which
  3. dissolutionwas then dissolved in ethyl acetate (500 ml)
  4. washwashed with water (500 ml)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationConcentration and trituration in hexane

Sources & evidence

ORD record
ord-9fe54b85deac41519544e2cdc7b1b483
Source dataset
uspto-grants-1996_11
Patent number
US05574056

Reaction notes

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