Trifluoroacetic acid → Trifluoroacetic acid

HRID 2403069Notes

Reaction equation

HRID 2403069 reaction equation
[C:1]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])(=[O:4])[CH:2]=[CH2:3].[F:10][C:11]([F:16])([F:15])[C:12]([OH:14])=[O:13]>ClCCl>[C:1]([OH:5])(=[O:4])[CH:2]=[CH2:3].[CH3:7][C:6]([O:5][C:1]([CH:2]=[CH2:3])=[O:4])([CH3:9])[CH3:8].[F:10][C:11]([F:16])([F:15])[C:12]([OH:14])=[O:13]

Participants

6

Reactant 2

HCID 6422Trifluoroacetic acidHCID 15458tert-Butyl acrylate2×

Product 3

HCID 6422Trifluoroacetic acidHCID 6581Acrylic AcidHCID 15458tert-Butyl acrylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The multi-arm acrylic acid star polymer was synthesized and reported in FIG. 4. For example, the tert-butyl acrylate star polymer from Example 2 (2.50 g, 19.5 mmol) was dissolved in 200 mL of dichloromethane, and 75 mL of trifluoroacetic acid (TFA, 975 mmol) was then added. The mixture was stirred vigorously until the generation of white precipitate ceased. The precipitate was filtered and washed with dichloromethane and diethyl ether, and then dried under reduced pressure overnight. Treatment of the poly(tert-butyl acrylate) star polymers of different molecular weights with TFA acid in dichloromethane yielded the corresponding acid star polymers. The molecular structures and weights of the resulting polymers (FIG. 4) were determined by 1H-NMR and SEC (see Example 7), respectively. 1H-NMR (CDCl3, 400 MHz): 1H-NMR (CDCl3, 400 MHz): δ=4.66 (q, 8H), 4.30 (q, 4H), 4.14 (q, 8H), 2.25 (brs), 1.86 (brs), 1.65-1.27 (brs, overlap), 1.30 (t, 12H). In this example, n may range from 2 to 500, but is typically between about 2 and 30.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with dichloromethane and diethyl ether
  3. customdried under reduced pressure overnight

Sources & evidence

ORD record
ord-d2459794b62d4752947ec8850e5f9a1b
Source dataset
uspto-grants-2014_08
Patent number
US08802235B2

Reaction notes

Loading…