Triethylamine → 3,3-Dimethoxy-2,2-dimethylpropyl methacrylate

HRID 1607703Notes

Reaction equation

HRID 1607703 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][CH:10]([O:16][CH3:17])[C:11]([CH3:15])([CH3:14])[CH2:12][OH:13].[C:18](Cl)(=[O:22])[C:19]([CH3:21])=[CH2:20]>C(Cl)Cl>[C:18]([O:13][CH2:12][C:11]([CH3:15])([CH3:14])[CH:10]([O:16][CH3:17])[O:9][CH3:8])(=[O:22])[C:19]([CH3:21])=[CH2:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 110080703,3-Dimethoxy-2,2-dimethylpropan-1-ol

Product 1

HCID 198225843,3-Dimethoxy-2,2-dimethylpropyl methacrylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 500 ml four-neck round bottom flask equipped with a mechanical stirrer, condenser thermometer and addition funnel were added 21.24 g triethylamine, 29.8 g 3,3-dimethoxy-2,2 dimethylpropanol, and 180 ml methylene chloride. The temperature was reduced to about 0° C. to -5° C. A total of 24.6 g methacryloyl chloride was added dropwise through an addition funnel. While maintaining the temperature at about 0° to -5° C., the mixture was then allowed to warm to room temperature and stirred for 30 min, and added to an equal volume (180 ml) of ice-water. The methylene chloride layer was separated from the aqueous layer, a small amount of anhydrous magnesium sulfate (3 g) was added, the solution was filtered, and methylene chloride was stripped off to isolate the product. Purification was done by as above at 65.2° C. under 0.5 mm Hg pressure.

Workup

  1. customTo a 500 ml four-neck round bottom flask equipped with a mechanical stirrer, condenser thermometer and addition funnel
  2. customwas reduced to about 0° C. to -5° C
  3. temperatureWhile maintaining the temperature at about 0° to -5° C.
  4. customThe methylene chloride layer was separated from the aqueous layer
  5. additiona small amount of anhydrous magnesium sulfate (3 g) was added
  6. filtrationthe solution was filtered
  7. customto isolate the product
  8. customPurification
  9. customwas done by as above at 65.2° C. under 0.5 mm Hg pressure

Sources & evidence

ORD record
ord-d3b73e834df346c3b66de3f0b4b5b17c
Source dataset
uspto-grants-1989_09
Patent number
US04866151

Reaction notes

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