Water → Benzyl 2-Benzylacrylate

HRID 1595156Notes

Reaction equation

HRID 1595156 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-2c749d11038f401daa5e1c5bf241efa8
Source dataset
uspto-grants-2001_09
Patent number
US06288046B1

Reaction notes

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