(Dimethylamino)ethyl methacrylate → p-Toluenesulfonic acid

HRID 2399178Notes

Reaction equation

HRID 2399178 reaction equation
CC(C(OCCN(C)C)=O)=C.O.[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19]([OH:22])(=[O:21])=[O:20])=[CH:15][CH:14]=1>C1(C)C=CC=CC=1>[CH3:23][C:13]1[CH:18]=[CH:17][C:16]([S:19]([OH:22])(=[O:21])=[O:20])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 17869(Dimethylamino)ethyl methacrylate2×HCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 6101p-Toluenesulfonic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a 50 milliliter Erlenmeyer flask were added 12.24 grams of the AB diblock copolymer toluene solution (49 weight percent of solids) prepared as described in Example I. This solution contained 6.0 grams of AB diblock copolymer. The AB diblock copolymer in this solution was found to contain 19.5 weight percent of DMAEMA repeat units (1H-NMR) which amounts to 1.17 grams or 0.00744 mole of DMAEMA repeat units. To this solution were added 1.39 grams of p-toluene sulfonic acid monohydrate (p-TSA) (0.00722 mole) which was rinsed into the flask with 2 to 3 milliliters of methanol and 7 to 8 milliliters of toluene. The charged mole percent ratio of p-TSA to DMAEMA repeat units was 97 percent so that nearly all of the DMAEMA repeat units have been targeted for conversion to the p-TSA protonated charge director. After magnetically stirring for 2 to 3 hours at ambient temperature, the solution was mixed with 587.8 grams of NORPAR 15™ and the resulting cloudy mixture was rotoevaporated at 40 to 50 millimeters Hg at 40° to 45° C. for 1 hour to remove the low boiling methanol and toluene solvents.

Workup

  1. customprepared
  2. washwas rinsed into the flask with 2 to 3 milliliters of methanol and 7 to 8 milliliters of toluene
  3. additionprotonated charge director
  4. additionthe solution was mixed with 587.8 grams of NORPAR 15™
  5. waitthe resulting cloudy mixture was rotoevaporated at 40 to 50 millimeters Hg at 40° to 45° C. for 1 hour
  6. customto remove the

Sources & evidence

ORD record
ord-64072999a8a049be8d531d2de8d2ba26
Source dataset
uspto-grants-1995_09
Patent number
USH0001483

Reaction notes

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