5-(HYDROXYMETHYL)-2-METHYL-3-FUROIC ACID synthesis

5synthesis methods

Product Name:5-(HYDROXYMETHYL)-2-METHYL-3-FUROIC ACID
CAS Number:15341-68-1
Molecular formula:C7H8O4
Molecular Weight:156.14

3-Furancarboxylic acid, 5-(hydroxymethyl)-2-methyl-, ethyl ester

15341-70-5
0 suppliers
inquiry

5-(HYDROXYMETHYL)-2-METHYL-3-FUROIC ACID

15341-68-1
11 suppliers
inquiry

Yield:15341-68-1 95%

Reaction Conditions:

with ethanol;sodium hydroxide at 60; for 5.5 h;

Steps:

5-Hydroxymethyl-2-methylfuran-3-carboxylic acid (39)

To a solution of 38 (1 .64 g, 9.01 mmol) in MeOH, NaBH₄ (682 mg, 18.02 mmol) was added. The mixture was stirred at room temperature for 30 min. The mixture was neutralized with citric acid. After evaporation of solvent, the residue was diluted with CH₂CI₂ and washed with water. The organic phases were dried, filtered and concentrated to give ethyl 5-hydroxymethyl-2-methylfuran-3-carboxylic ester (1 .39 g, 7.54 mmol, 84 %, MW: 184.191 ) as a white solid. IR (v cm ¹) 3423 (OH), 1710 (C=0). ¹H NMR (300 MHz, CDCI₃, δ ppm, J Hz) δ 6.52 (s, 1 H, H-3), 4.53 (s, 1 H, H-f), 4.26 (q, 2H, ²J_H,H = 6.9, - CH₂CH₃), 2.55 (s, 3H, Me), 1 .33 (t, 3H, -CH₂CH₃). ¹³C NMR (75.4 MHz, CDCI₃, δ ppm) δ 177.2 (CHO), 164.8 (COOEt), 162.7 (C-5), 150.4 (C-2), 122.6 (C-3), 1 16.6 (C-4), 61 .0 (- CH₂CH₃), 14.4 (Me), 14.4 (-CH₂CH₃). CIMS m/z 185 [46%, (M+H)⁺], 184 [61 %, (M)⁺], 167 [100%, (M-OH+H)⁺]. HRCIMS m/z found 184.0732, calc. for C₉H₁₂0₄: 184.0736. This ester (1 .36 mg, 7.41 mmol) was dissolved in 1 M NaOH/EtOH (30 mL) and the mixture was stirred at 60^QC for 5.5 h. The mixture was cooled to 0 ^QC, neutralized with acid resin IR 120 (H+), filtered and concentrated to give 39 (1 .1 Og, 7.04 mmol, 95 %, MW: 156.137) as a white solid. IR (v cm ¹) 3330 (OH), 1665 (C=0). ¹H NMR (300 MHz, MeOD, δ ppm, J Hz) δ 6.50 (s, 1 H, H-3), 4.45 (s, 1 H, H-1 '), 2.54 (s, 3H, Me). ¹³C NMR (75.4 MHz, MeOD, δ ppm) δ 167.3 (-COOH), 160.4 (C-5), 154.1 (C-2), 1 15.4 (C-4), 109.4 (C-3), 57.1 (C-f), 13.7 (Me). CIMS m/z 158 [63%, (M+2H)⁺], 157 [65%, (M+H)⁺], 139 [100%, (M-OH+H)⁺]. HRCIMS m/z found 157.0501 , calc. for C₇H₉0₄: 157.0501 .