2-Benzylacrylic Acid → Methyl 2-benzylprop-2-enoate

HRID 847617Notes

Reaction equation

HRID 847617 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:13]([O-])(O)=O.[Na+]>CO>[CH2:1]([C:8](=[CH2:12])[C:9]([O:11][CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 3035712-Benzylacrylic AcidHCID 516892Sodium Bicarbonate

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

a-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) δ 7.17-7.35 (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-ef4685cf3a4f489d8d88bdcb7988193e
Source dataset
uspto-grants-1992_08
Patent number
US05142056

Reaction notes

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