Pyridine → 4-Methoxy cinnamic acid

HRID 1762715Notes

Reaction equation

HRID 1762715 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>C1COCC1>[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 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

11.3 g of D-panthenol (0.055 mol) are placed in 100 ml of THF while gassing with argon in a 500 ml 4-necked sulphonation flask provided with a thermometer, a 100 ml dropping funnel, a magnetic stirrer and a reflux condenser. A solution of 27.8 g of 4-methoxycinnamic acid chloride (0.14 mol) in 100 ml of tetrahydrofuran is then added dropwise within about 15 minutes. A solution of 11.1 g of pyridine (0.14 mol) is now added dropwise within about 30 minutes and the mixture is stirred for a further 3 hours. The precipitate is filtered off under suction and the filtrate is concentrated on a rotary evaporator. The residue is dissolved in 300 ml of CH2Cl2. This solution is washed with 2× 60 ml of 5% HCl and then with 2× 60 ml of 5% NaHCO3. After drying (Na2SO4) the organic phase is concentrated on a rotary evaporator. The yellow, viscous residue (33.8 g) is chromatographed (toluene/ethyl acetate, 8:2) on 1 kg of silica gel (0.04-0.063 mm) under 0.5 bar pressure. There are obtained 15.9 g of yellowish <R>-panthenol diester of p-methoxycinnamic acid (yield 55%).

Workup

  1. customwhile gassing with argon in a 500 ml 4-necked sulphonation flask
  2. customprovided with a thermometer
  3. filtrationThe precipitate is filtered off under suction
  4. concentrationthe filtrate is concentrated on a rotary evaporator
  5. dissolutionThe residue is dissolved in 300 ml of CH2Cl2
  6. washThis solution is washed with 2× 60 ml of 5% HCl
  7. dry with materialAfter drying (Na2SO4) the organic phase
  8. concentrationis concentrated on a rotary evaporator
  9. customThe yellow, viscous residue (33.8 g) is chromatographed (toluene/ethyl acetate, 8:2) on 1 kg of silica gel (0.04-0.063 mm) under 0.5 bar pressure

Sources & evidence

ORD record
ord-63dc6a22469a44f891efb0cff83fbce6
Source dataset
uspto-grants-1989_05
Patent number
US04833259

Reaction notes

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