Phenothiazine → 2,2-Dimethyl-5-(4-vinylbenzyl)-1,3-dioxane-4,6-dione

HRID 552034Notes

Reaction equation

HRID 552034 reaction equation
[CH3:1][C:2]1([CH3:11])[O:7][C:6](=[O:8])[CH:5]([CH3:9])[C:4](=[O:10])[O:3]1.ClC[C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[CH2:19])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].C1C2NC3C(=CC=CC=3)SC=2C=CC=1>C(OCC)(=O)C.CC(C)=O>[CH3:11][C:2]1([CH3:1])[O:3][C:4](=[O:10])[CH:5]([CH2:9][C:14]2[CH:21]=[CH:20][C:17]([CH:18]=[CH2:19])=[CH:16][CH:15]=2)[C:6](=[O:8])[O:7]1

Participants

7

Reactant 4

HCID 7108PhenothiazineHCID 11430Potassium CarbonateHCID 74126p-Vinylbenzyl chlorideHCID 772992,2,5-Trimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 224573552,2-Dimethyl-5-(4-vinylbenzyl)-1,3-dioxane-4,6-dioneYield 21.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a 500 mL 3-necked round bottomed flask equipped with a stir bar, thermowell, and a condenser connected to a nitrogen line was added 10.0 g (0.0632 mole) of 2,2,5-trimethyl-1,3-dioxane-4,6-dione, 10.6 g (0.0632 mol) of p-(chloromethyl)styrene, 35 g (0.2528 mol) of potassium carbonate and 200 mL of acetone. Approximately 1 g of phenothiazine was added as a stabilizer. The mixture was refluxed with stirring overnight at which time it was allowed to cool, diluted with 200 mL of ethyl acetate and filtered through a bed of Celite. The filtrate was washed with water and brine and dried overnight over anhydrous sodium sulfate. The suspension was filtered and the filtrate evaporated on a rotary evaporator to a light brown oil which spontaneously crystallized. The crystals were collected and washed with 35-65 petroleum ether to yield 3.5 g of 2,2-dimethyl-5-(4-vinylbenzyl)-1,3-dioxane-4,6-dione as shown by formula (III).

Workup

  1. customTo a 500 mL 3-necked round bottomed flask equipped with a stir bar
  2. customthermowell, and a condenser connected to a nitrogen line
  3. temperatureThe mixture was refluxed
  4. temperatureto cool
  5. filtrationfiltered through a bed of Celite
  6. washThe filtrate was washed with water and brine
  7. dry with materialdried overnight over anhydrous sodium sulfate
  8. filtrationThe suspension was filtered
  9. customthe filtrate evaporated on a rotary evaporator to a light brown oil which
  10. customspontaneously crystallized
  11. customThe crystals were collected
  12. washwashed with 35-65 petroleum ether

Sources & evidence

ORD record
ord-490d5c8e80d947c68dc014e525e2d0d9
Source dataset
uspto-grants-2011_05
Patent number
US07951525B2

Reaction notes

Loading…