Pyridine → 55226-78-3

HRID 1691521Notes

Reaction equation

HRID 1691521 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[C:14](OC(=O)C)(=[O:16])[CH3:15].N1C=CC=CC=1>>[C:14]([O:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:7]=1)(=[O:16])[CH3:15]

Participants

4

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 5319562Methyl-P-Coumarate

Product 1

HCID 123984255226-78-3Yield 93.1%

Procedure

To a solution of methyl (2E)-3-(4-hydroxyphenyl)acrylate (5.35 g, 30.0 mmol) in acetic anhydride (45.0 mL, 476 mmol) was added pyridine (4.85 mL, 60.0 mmol), and the mixture was stirred at room temperature for 26 hr. The reaction mixture was concentrated under reduced pressure. Water was added to the residue, and the mixture was extracted with diethyl ether. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The precipitated crystals were washed with ethyl acetate-hexane to give the title compound (6.15 g, yield 93%) as colorless crystals.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionWater was added to the residue
  3. extractionthe mixture was extracted with diethyl ether
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washThe precipitated crystals were washed with ethyl acetate-hexane

Sources & evidence

ORD record
ord-b0bac99f99484d20a0ac371d785a716d
Source dataset
uspto-grants-2012_04
Patent number
US08153694B2

Reaction notes

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