Benzyl Bromide → Benzyl 2-Benzylacrylate

HRID 1292293Notes

Reaction equation

HRID 1292293 reaction equation
[CH2:1]=[C:2]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4].C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(OCC)(=O)C>CN(C)C=O>[CH2:1]=[C:2]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([O:5][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:4]

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 3035712-Benzylacrylic Acid

Product 1

HCID 10912012Benzyl 2-BenzylacrylateYield 60.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

The title acid of Step 9 (5.2 g, 30 mmol) was dissolved in dimethylformamide (25 mL) and cooled to 0° C. To this potassium carbonate (5.7 g, 41.48 mmol) was added followed by benzyl bromide (5.7 g, 29.7 mmol). The mixture was stirred at room temperature overnight. The mixture was filtered and the filtrate was diluted with ethyl acetate, washed with 3 times of water, brine. The solution was dried (Na2 SO4) and evaporated. The residue was purified by flash chromatography on silica gel, eluting with 90:10 heptane:ethyl acetate to give the pure title compound as colorless oil (4.5 g, 60% yield). 1H NMR: 300 MHz spectrum consistent with proposed structure. Anal: calcd. for C17 H16O2 : C, 80.93; H, 6.39. Found: C, 80.69; H 6.47.

Workup

  1. filtrationThe mixture was filtered
  2. additionthe filtrate was diluted with ethyl acetate
  3. washwashed with 3 times of water, brine
  4. customThe solution was dried (Na2 SO4)
  5. customevaporated
  6. customThe residue was purified by flash chromatography on silica gel
  7. washeluting with 90:10 heptane

Sources & evidence

ORD record
ord-42db68c624b94d65876f28be8b953ae1
Source dataset
uspto-grants-1998_05
Patent number
US05756549

Reaction notes

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