Boron trifluoride etherate → Methyl 2-benzylprop-2-enoate

HRID 973506Notes

Reaction equation

HRID 973506 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.B(F)(F)F.[CH3:17]COCC.C([O-])(O)=O.[Na+]>CO>[CH2:1]([C:8](=[CH2:12])[C:9]([O:11][CH3:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 3035712-Benzylacrylic AcidHCID 516892Sodium Bicarbonate

Product 1

HCID 575761Methyl 2-benzylprop-2-enoateYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

α-Benzylacrylic acid (1.00 g, 6.17 mmol) in methanol (20 ml) was treated with BF3.Et2O (2 ml). The mixture was heated to reflux for 14 h, cooled, and poured into saturated NaHCO3 solution. Extraction with ether followed by drying over Na2SO4 and evaporation afforded 1.03 g (95%) of a mobile oil. 1H NMR (CDCl3) δ7.17-7.35 (m,5H), 6.23 (m,1H), 5.47 (m,1H), 3.74 (s,3H), 3.63 (s,2H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 14 h
  3. temperaturecooled
  4. extractionExtraction with ether
  5. dry with materialby drying over Na2SO4 and evaporation

Sources & evidence

ORD record
ord-c014e809fb19466ba17976d2e4ee50e7
Source dataset
uspto-grants-1991_11
Patent number
US05063208

Reaction notes

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