Boron trifluoride etherate → Methyl-P-Coumarate

HRID 1435561Notes

Reaction equation

HRID 1435561 reaction equation
B(F)(F)F.[CH3:5]COCC.[CH:10]1[C:15](/[CH:16]=[CH:17]/[C:18]([OH:20])=[O:19])=[CH:14][CH:13]=[C:12]([OH:21])[CH:11]=1>CO>[C:18]([O:20][CH3:5])(=[O:19])/[CH:17]=[CH:16]/[C:15]1[CH:14]=[CH:13][C:12]([OH:21])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 637542P-Coumaric Acid

Product 1

HCID 5319562Methyl-P-CoumarateYield 74.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

Boron trifluoride etherate (0.067 mol) is added to a solution of coumaric acid (0.034 mol) in methanol (50 ml) in a 250 ml round bottom flask and the mixture stirred at 70° C. for 2 hours and evaporated to dryness under reduced vacuum. The residual solid is taken up in CH2Cl2, washed with aqueous NaHCO3, dried over MgSO4 and filtered to provide, after evaporation of the CH2Cl2, the desired product as a pale yellow solid in 74.1% yield.

Workup

  1. customevaporated to dryness under reduced vacuum
  2. washwashed with aqueous NaHCO3
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customto provide
  6. customafter evaporation of the CH2Cl2

Sources & evidence

ORD record
ord-d41623f879ef4050a0eb72614c324fcd
Source dataset
uspto-grants-2009_11
Patent number
US07618697B2

Reaction notes

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