ChemicalBook CAS DataBase List 5-PHENOXY-2-FUROIC ACID

5-PHENOXY-2-FUROIC ACID synthesis

6synthesis methods

Product Name:5-PHENOXY-2-FUROIC ACID
CAS Number:60698-32-0
Molecular formula:C11H8O4
Molecular Weight:204.18

645-12-5 Synthesis

645-12-5
144 suppliers
$17.00/1g

108-95-2 Synthesis

108-95-2
727 suppliers
$14.00/25g

60698-32-0
24 suppliers
$167.00/1g

Yield:60698-32-0 87%

Reaction Conditions:

with NaH;sulfuric acid in ethanol;dimethyl sulfoxide;

Steps:

36.1 Step 1

Step 1 Preparation of 5-phenoxy-2-furoic acid A flask was charged with 5-nitro-2-furoic acid (15.02 g, 95.62 mmol), absolute ethanol (100 mL), and concentrated sulfuric acid (1 mL) and refluxed overnight. After cooling the reaction mixture, the volatiles were removed under vacuum, the resulting slurry taken up into ethyl acetate, and washed sequentially (1*, NaHCO₃; 1*, brine), dried (MgSO₄), filtered and concentrated under vacuum to provide the corresponding ester as a light yellow solid (15.31 g, 87%) which was used without further purification. A flask was charged with NaH (2.9 g, 96.7 mmol, 80% suspension in oil), and dimethylsulfoxide (DMSO)(200 mL), and flushed with nitrogen. To this solution was added neat phenol (9.1 g, 96.7 mmol) in a portionwise fashion; the reaction was stirred under nitrogen until gas evolution ceased. A solution of 5-nitro-2-furoic acid (14.92 g, 80.6 mmol) in DMSO (120 mL) was then added to the reaction to give a dark purple solution which was judged to be complete by thin layer chromatography after 0.5 h. The reaction was poured into saturated aqueous NaHCO₃ extracted with ethyl acetate (3*).

References:

US5214204,1993,A