Hydrochloric Acid → 2-Furanacrylic acid

HRID 2389863

Reaction equation

HRID 2389863 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 6434022-Furanacrylic acidYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 2-furfural (500 g, 5.20 mol) and malonic acid (595 g, 5.72 mol) in pyridine (500 mL) was added piperidine (50 mL, 0.505 mol) at room temperature, and the mixture was stirred at 100° C. for 3 hr. The reaction solution was poured into water (1 L) and acidified with 6M hydrochloric acid. The resulting precipitate was collected by filtration to give the title compound (660 g, yield 92%).

Workup

  1. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-f4f5782bb6ab4fe5b912f3315f5b6e9d
Source dataset
uspto-grants-2012_09
Patent number
US08273761B2

Linked notes

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