ChemicalBook CAS DataBase List 4-Acryloylmorpholine

4-Acryloylmorpholine synthesis

10synthesis methods

Product Name:4-Acryloylmorpholine
CAS Number:5117-12-4
Molecular formula:C7H11NO2
Molecular Weight:141.17

A solution of 0.04 mol of the corresponding amine in 20 ml of anhydrous methylene chloride was slowly added at 0-5°C to 0.02 mol of acryloyl chloride in 20 ml of anhydrous methylene chloride. The mixture was stirred for 3 h at room temperature in an inert atmosphere, and the precipitate was filtered off and washed with methylene chloride (2 × 10 ml). The organic layer was washed in succession with 5 ml of water and 5 ml of a saturated solution of NaHCO3 and dried over Na2SO4, the solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel using hexane-ethyl acetate (5 : 1 to 1 : 1) as eluent. 4-Acryloylmorpholine, Yield 1.78 g (63%). IR spectrum, ν, cm-1: 2857, 1647, 1612, 1439, 1263, 1238, 1115, 1038, 953. 1H NMR spectrum, δ, ppm: 3.51-3.73 m (8H, NCH2CH2O), 5.72 d.d (1H, 3-Hcis, 3J = 10.6, 2J = 1.9 Hz), 6.29 d.d (1H, 3-Htrans, 3J = 16.7, 2J = 1.9 Hz), 6.57 d.d (1H, 2-H, J = 16.7, 10.6 Hz). 13C NMR spectrum, δC, ppm: 41.74 and 45.66 (CH2N), 66.22 (CH2O), 126.64 (C2), 127.69 (C3), 164.92 (C1). Mass spectrum, m/z (Irel, %): 141 (36) [M]+, 140 (12), 126 (58), 112 (22), 111 (15), 110 (15), 109 (12), 98 (10), 96 (26), 86 (72), 83 (13), 70 (14), 68 (14), 57 (17), 56 (86), 55 (100), 42 (23).

Fig. The synthetic method 2 of 4-Acryloylmorpholine

1-Propanone, 3-methoxy-1-(4-morpholinyl)-

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Yield:5117-12-4 96%

Reaction Conditions:

with sodium methoxide;4-methoxy-phenol at 200;Pyrolysis;

Steps:

10.c

(C) Into a 1000 mL four-necked flask equipped with a stirrer, a thermometer, and a gas introduction line,400 g of Meo-DEAA obtained in the step (b)6.8 g of potassium hydroxide and 0.4 g of TDA were added.Thereafter, a flask was equipped with a distillation column equipped with a packing material, a condenser and a distillation receiver, a trace nitrogen gas was flowed as a carrier,While stirring the reaction solution, the pot temperature was adjusted to 180 ° C. and the degree of vacuum was adjusted to 60 kPa,The pyrolysis reaction was carried out for 12 hours,307 g (purity = 93%, yield = 92%) of crude N, N-diethylacrylamide (DEAA) was obtained from a water condenser.Further, the obtained crude DEAA was transferred to a distillation purification apparatus equipped with a 20 cm McMahon packing (size 6 mm) packed tower and purified by distillation under reduced pressure (60 ° C./0.13 kPa)As a colorless liquid, 258 g of high purity product DEAA (purity 99.8%) was obtained. Examples 2 to 18 In Example 1,The starting materials, the catalyst, the solvent, the polymerization inhibitor and the reaction conditions of each step were changed as shown in Table 1, and synthesis was carried out in the same manner as in Example 1 to obtain the respective target compound.The results are shown in Table 2.

References:

JP2015/101554,2015,A Location in patent:Paragraph 0057; 0060

30668-14-5 Synthesis