Pyridine → 4-Methoxy cinnamic acid

HRID 1762716Notes

Reaction equation

HRID 1762716 reaction equation
[OH:1]CCCNC(=O)[C@H](C(CO)(C)C)O.[CH3:15][O:16][C:17]1[CH:27]=[CH:26][C:20]([CH:21]=[CH:22][C:23](Cl)=[O:24])=[CH:19][CH:18]=1.N1C=CC=CC=1>C(OC)(=O)C>[CH3:15][O:16][C:17]1[CH:27]=[CH:26][C:20]([CH:21]=[CH:22][C:23]([OH:1])=[O:24])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 5748487L-PanthenolHCID 534017724-Methoxycinnamic acid chloride

Product 1

HCID 132454-Methoxy cinnamic acidYield 86%

Reagents, catalysts & solvents 1

HCID 6584Methyl AcetateSolvent2×

Procedure

17.4 g of D-panthenol )0.085 mol) are placed in 300 ml of methyl acetate while gassing with argon in a 750 ml 4-necked sulphonation flask provided with a thermometer, a 100 ml dropping funnel, a magnetic stirrer and a reflux condenser. A solution of 75.5 g of 4-methoxycinnamic acid chloride (0.38 mol) in 150 ml of methyl acetate is then added dropwise within about 20 minutes. A solution of 33.6 g of pyridine (0.425 mol) is added dropwise within about 40 minutes. The reaction mixture is finally heated to reflux temperature for 4 hours. After cooling the precipitate is filtered off under suction. The filtrate is washed with 2× 150 ml of 5% HCl and then with 2× 100 ml of water. After drying over Na2SO4 the organic phase is concentrated on a rotary evaporator. The yellow, viscous residue (74.2 g) is chromatographed (toluene/ethyl acetate, 7:1) on 1 kg of silica gel (0.040-0.063 mm) under 0.5 bar pressure. There are obtained 50.1 g of yellow <R>-panthenol triester of p-methoxycinnamic acid (yield 86%).

Workup

  1. customwhile gassing with argon in a 750 ml 4-necked sulphonation flask
  2. customprovided with a thermometer
  3. temperatureThe reaction mixture is finally heated
  4. temperatureto reflux temperature for 4 hours
  5. temperatureAfter cooling the precipitate
  6. filtrationis filtered off under suction
  7. washThe filtrate is washed with 2× 150 ml of 5% HCl
  8. dry with materialAfter drying over Na2SO4 the organic phase
  9. concentrationis concentrated on a rotary evaporator
  10. customThe yellow, viscous residue (74.2 g) is chromatographed (toluene/ethyl acetate, 7:1) on 1 kg of silica gel (0.040-0.063 mm) under 0.5 bar pressure

Sources & evidence

ORD record
ord-af803b853e194c58946d08d340563d01
Source dataset
uspto-grants-1989_05
Patent number
US04833259

Reaction notes

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