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

HRID 1593920Notes

Reaction equation

HRID 1593920 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.)
  6. distillationThe residue was 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-33caa6e1a30949528023136a2a513e01
Source dataset
uspto-grants-2007_11
Patent number
US07300739B2

Reaction notes

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