Water → Benzyl 2-Benzylacrylate

HRID 1005303Notes

Reaction equation

HRID 1005303 reaction equation
[CH2:1]([C:8](=[CH2:12])[C:9]([OH:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].O.[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C)C=O>[CH2:1]([C:8](=[CH2:12])[C:9]([O:11][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 3035712-Benzylacrylic Acid

Product 1

HCID 10912012Benzyl 2-BenzylacrylateYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-benzylacrylic acid (1.02 g, 6.3 mmol) in dimethylformamide (10 ml) was added potassium carbonate (1.04 g, 7.6 mmol) and water (0.25 ml) with stirring. After 10 minutes, benzyl bromide (0.9 ml, 7.6 mmol) was added. After 3 hours, water was added and the resulting mixture was extracted with ether. The ether layer was washed 3 times with water, dried over magnesium sulfate, filtered over silica gel, and concentrated under reduced pressure. The resulting oil was distilled (70° C., 0.2 torr) to remove any unreacted starting material, then distilled (125° C., 0.2 torr) to yield 1.38 g (87%) of clear oil. 1H NMR (CDCl3): δ 3.7 (s, 2H), 5.2 (s, 2H), 5.5 (s, 1H), 6.3 (s, 1H), 7.2-7.6 (m, 10H).

Workup

  1. waitAfter 3 hours
  2. extractionthe resulting mixture was extracted with ether
  3. washThe ether layer was washed 3 times with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered over silica gel
  6. concentrationconcentrated under reduced pressure
  7. distillationThe resulting oil was distilled (70° C., 0.2 torr)
  8. customto remove
  9. distillationdistilled (125° C., 0.2 torr)

Sources & evidence

ORD record
ord-d6b921a2681a4602b887a55760ea544b
Source dataset
uspto-grants-2000_04
Patent number
US06054444

Reaction notes

Loading…