Vinyl Acetate → Vinyl 4-(pyren-1-yl)butanoate

HRID 2194326Notes

Reaction equation

HRID 2194326 reaction equation
[C:1]1([CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])[C:14]2[C:15]3=[C:16]4[C:11](=[CH:12][CH:13]=2)[CH:10]=[CH:9][CH:8]=[C:7]4[CH:6]=[CH:5][C:4]3=[CH:3][CH:2]=1.[C:23](OC=C)(=O)[CH3:24]>C1(C)C=CC=CC=1>[C:1]1([CH2:17][CH2:18][CH2:19][C:20]([O:22][CH:23]=[CH2:24])=[O:21])[C:14]2[C:15]3=[C:16]4[C:11](=[CH:12][CH:13]=2)[CH:10]=[CH:9][CH:8]=[C:7]4[CH:6]=[CH:5][C:4]3=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 7904Vinyl Acetate2×HCID 769771-Pyrenebutanoic acid

Product 1

HCID 86648107Vinyl 4-(pyren-1-yl)butanoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

To a 500 mL, two neck flask equipped with a stir bar, argon inlet, and stopper is added 4-(1-Pyrenyl)butyric acid (10.0 grams, 34.7 mmol, obtained from Sigma-Aldrich, Milwaukee, Wis.), palladium acetate 1,10-phenanthroline complex (403 milligrams, 1 mmol) and vinyl acetate (128 milliliters, 1.39 mol, obtained from Sigma-Aldrich, Milwaukee, Wis.). Next, toluene (200 milliliters) is added, the solution is purged with argon and stirred magnetically at 60° C. for 62 hours. The excess vinyl acetate, along with acetic acid (co-product) is removed, an additional vinyl acetate (32 mL, 0.35 mol) is added, and the reaction is continued for 48 hours at 60° C. under argon to complete the reaction. The excess vinyl ester is removed, and the crude product is filtered to remove suspended catalyst residue, and the toluene is removed in vacuo to famish vinyl 4-(pyren-1-yl)butanoate.

Workup

  1. customTo a 500 mL, two neck flask equipped with a stir bar, argon inlet
  2. customthe solution is purged with argon
  3. customThe excess vinyl acetate, along with acetic acid (co-product) is removed
  4. waitthe reaction is continued for 48 hours at 60° C. under argon
  5. customthe reaction
  6. customThe excess vinyl ester is removed
  7. filtrationthe crude product is filtered
  8. customto remove
  9. customthe toluene is removed in vacuo to famish vinyl 4-(pyren-1-yl)butanoate

Sources & evidence

ORD record
ord-83c7edf7d9ca4a1985a106b167cd6f67
Source dataset
uspto-grants-2012_12
Patent number
US08334026B2

Reaction notes

Loading…