Hydrochloric Acid → Furylacrylic acid

HRID 734302Notes

Reaction equation

HRID 734302 reaction equation
[CH:1]1[CH:5]=[C:4]([CH:6]=O)[O:3][CH:2]=1.C(O)(=O)[CH2:9][C:10]([OH:12])=[O:11].N1CCCCC1.Cl>N1C=CC=CC=1.O>[O:3]1[CH:2]=[CH:1][CH:5]=[C:4]1[CH:6]=[CH:9][C:10]([OH:12])=[O:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 7362FurfuralHCID 8082Piperidine

Product 1

HCID 10876Furylacrylic acidYield 81.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

The mixture of 2-furfural (15 g, 0.15 mol), malonic acid (17.9 g, 0.17 mol) and piperidine(1.5 ml, 0.016 mol) in 80 ml of pyridine was stirred for 5 hours at 100° C. and then refluxed for 20 min, which was cooled down to room temperature and poured into water (180 ml), and resultant mixture was acidified with concentrated HCl. The generated precipitate was collected by filtration and dried under the reduced pressure to give 3-(furan-2-yl)-acrylic acid (16.8 g). 1H NMR (400 MHz, DMSO-d6) ppm 12.44 (brs, 1H), 7.83 (d, J=1.8 Hz, 1H), 7.40 (d, J=15.9 Hz, 1H), 6.93 (d, J=3.3 Hz, 1H), 6.63 (dd, J=1.8, 3.3 Hz, 1H), 6.17 (d, J=15.7 Hz, 1H).

Workup

  1. temperaturerefluxed for 20 min
  2. temperaturewhich was cooled down to room temperature
  3. filtrationThe generated precipitate was collected by filtration
  4. customdried under the reduced pressure

Sources & evidence

ORD record
ord-9562c49a54984bd28694d2402e737b2d
Source dataset
uspto-grants-2009_09
Patent number
US07592352B2

Reaction notes

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