(Dimethylamino)ethyl methacrylate → Methacrylic Acid

HRID 440425Notes

Reaction equation

HRID 440425 reaction equation
[C:1]([O:6][Si](C)(C)C)(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:11]([O:16][CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])(=[O:15])[C:12]([CH3:14])=[CH2:13].[C:22]([OH:27])(=[O:26])[C:23]([CH3:25])=[CH2:24].[CH3:28][CH2:29][O:30][CH:31]([OH:40])[CH2:32][O:33][CH2:34][CH2:35][O:36][CH2:37][CH2:38][OH:39].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:11]([O:16][CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])(=[O:15])[C:12]([CH3:14])=[CH2:13].[C:22]([OH:27])(=[O:26])[C:23]([CH3:25])=[CH2:24].[CH3:28][CH2:29][O:30][CH:31]([OH:40])[CH2:32][O:33][CH2:34][CH2:35][O:36][CH2:37][CH2:38][OH:39]

Participants

7

Reactant 4

HCID 17869(Dimethylamino)ethyl methacrylateHCID 2724141Tetrabutylammonium FluorideHCID 27338392-Propenoic acid, 2-methyl-, trimethylsilyl esterHCID 86746980b-Ethoxytriethylene glycol methacrylate

Product 3

HCID 4093Methacrylic AcidHCID 17869(Dimethylamino)ethyl methacrylateHCID 86746980b-Ethoxytriethylene glycol methacrylate

Procedure

The solution of poly(trimethylsilyl methacrylate [48 mol %]-b-2-phenylethyl methacrylate [30 mol %]-co-2-dimethylaminoethyl methacrylate [7 mol %]-b-ethoxytriethylene glycol methacrylate [15 mol %]) was treated with 45 mL of 0.03 M methanolic tetrabutylammonium fluoride and heated at reflux for 8 hr. The solution was evaporated in a rotary evaporator under reduced pressure. The residual polymer was dried for 24 hr in a vacuum oven to give 59 g of poly(methacrylic acid [48 mol %]-b-2-phenylethyl methacrylate [30 mol %]-co-2-dimethylaminoethyl methacrylate [7 mol %]-b-ethoxytriethylene glycol methacrylate [15 mol %]). 1H NMR analysis of the product showed that no trimethylsilyl ester groups remained.

Workup

  1. temperatureheated
  2. temperatureat reflux for 8 hr
  3. customThe solution was evaporated in a rotary evaporator under reduced pressure
  4. customThe residual polymer was dried for 24 hr in a vacuum oven

Sources & evidence

ORD record
ord-75b0818a08fe4aeab5e5cf7c66a2af4e
Source dataset
uspto-grants-1996_05
Patent number
US05519085

Reaction notes

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