ChemicalBook CAS DataBase List 2-ETHYLACRYLIC ACID 98

2-ETHYLACRYLIC ACID 98 synthesis

13synthesis methods

Product Name:2-ETHYLACRYLIC ACID 98
CAS Number:3586-58-1
Molecular formula:C5H8O2
Molecular Weight:100.12

50-00-0 Synthesis

50-00-0
868 suppliers
$10.00/25g

601-75-2 Synthesis

601-75-2
157 suppliers
$6.00/1g

3586-58-1
31 suppliers
$275.00/250mg

Yield: 95%

Reaction Conditions:

with diethylamine in ethyl acetate at 0; for 4 h;Reflux;

Steps:

4.7 2-Methylenebutanoic acid (15)
To a solution of 2-ethylmalonic acid (14, 1.50g, 11.35mmol) in EtOAc (114mL) cooled in an ice-water bath (0°C) was added dropwise Et₂NH (1.76mL, 17.01mmol) followed by addition of solid paraformaldehyde (682.0mg, 22.70mmol). The resultant mixture was stirred under refluxing for 4h. The reaction was quenched with water and the reaction mixture was adjusted to ca. pH 1 with concn. aqueous HCl. The resultant mixture was extracted with EtOAc (100mL×3) and the combined organic layer was washed with brine, dried over anhydrous Na₂SO₄, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, 50% EtOAc in hexane) to give 15¹² (1.08g, 95%) as a yellow oil. R_f=0.60 (25% EtOAc in hexane); ¹H NMR (400MHz, CDCl₃) δ 11.98 (br s, 1H), 6.25 (s, 1H), 5.61 (d, J=2.0Hz, 1H), 2.29 (qd, J=7.6, 0.8Hz, 2H), 1.06 (t, J=7.6Hz, 3H); ¹³C NMR (100MHz, CDCl₃) δ 173.2, 141.8, 125.9, 24.4, 12.6; HRMS (+CI) calcd for C₅H₉O₂ 101.0603 (M+H⁺), found 101.0607.