Phenothiazine → 2-Hydroxy-2,2-dimethylethyl methacrylate

HRID 229317Notes

Reaction equation

HRID 229317 reaction equation
ClC[CH2:3][C:4]([CH3:7])([OH:6])[CH3:5].[C:8]([O-:13])(=[O:12])[C:9]([CH3:11])=[CH2:10].[Na+].C1C2NC3C(=CC=CC=3)SC=2C=CC=1>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].C(#N)CCC.CCCCCC>[C:8]([O:13][CH2:3][C:4]([OH:6])([CH3:7])[CH3:5])(=[O:12])[C:9]([CH3:11])=[CH2:10]

Participants

7

Reactant 3

HCID 7108PhenothiazineHCID 5477654-Chloro-2-methylbutan-2-olHCID 3255932Sodium methacrylate

Product 1

HCID 99422122-Hydroxy-2,2-dimethylethyl methacrylate

Reagents, catalysts & solvents 3

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 8008ButyronitrileSolventHCID 8058HexaneSolvent

Procedure

A mixture of 1-chloromethyl-2-methyl-2-propanol (21.80 g, 0.20 mole), sodium methacrylate (32.40 g, 0.30 mole), Adogen 464 (7.00 g, 0.015 mole) (phase transfer catalyst purchased from Aldrich Chemical Co.), and phenothiazine (60 mg) in butyronitrile (200 ml) was heated to reflux under nitrogen in a three-necked round bottomed flask equipped with a condenser and a mechanical stirrer. After cooling the contents to room temperature, the mixture was diluted with hexane (200 ml) and filtered through celite. The solvents were removed under aspirator vacuum (40-80° C.) The residue was distilled under high vacuum. The 22.50 grams of the product was collected between 72-80° C. at 2 mm pressure as a clear liquid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under nitrogen in a three-necked round bottomed flask
  3. customequipped with a condenser and a mechanical stirrer
  4. filtrationfiltered through celite
  5. customThe solvents were removed under aspirator vacuum (40-80° C.) The residue
  6. distillationwas distilled under high vacuum
  7. customThe 22.50 grams of the product was collected between 72-80° C. at 2 mm pressure as a clear liquid

Sources & evidence

ORD record
ord-1103494114ac4e60811508b4aa8708a3
Source dataset
uspto-grants-2009_07
Patent number
US07563558B2

Reaction notes

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