ChemicalBook CAS DataBase List CIS-3-CHLOROACRYLIC ACID

CIS-3-CHLOROACRYLIC ACID synthesis

4synthesis methods

Product Name:CIS-3-CHLOROACRYLIC ACID
CAS Number:1609-93-4
Molecular formula:C3H3ClO2
Molecular Weight:106.51

471-25-0
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2345-61-1
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1609-93-4
49 suppliers
$40.00/100mg

Yield: 31% ， 40%

Reaction Conditions:

with thionyl chloride in N,N-dimethyl-formamide at 30; for 0.75 h;

Steps:

31.a a. synthesis of (E)-3-chloroacrylic acid
a. synthesis of (E)-3-chloroacrylic acid (0278) (0279) Propargyl acid (140 mg, 2 mmol) was dissolved in anhydrous DMF (1 mL), into which thionyl chloride (286 mg, 2.4 mmol) was added dropwise at a temperature below 30°C. After stirring for 45 min, the reaction mixture was evaporated to remove excessive thionyl chloride, poured into ice-water, extracted with diethyl ether, the organic phase was washed with water, dried over anhydrous Na₂SO₄, filtrated, concentrated, purified by column chromatography to deliver cis-3-chloroacrylic acid (121 mg, 40% yield) and trans-3-chloroacrylic acid (94 mg, 31% yield). (E)-3-chloroacrylic acid, ¹H-NMR (CDCl₃, 400 MHz, δ ppm): 9.24 (bs, 1H), 7.52 (d, J=13 Hz, 1H), 6.26 (d, J=13 Hz, 1H). (Z)-3-chloroacrylic acid, ¹H-NMR (CDCl₃, 400 MHz, δ ppm): 9.24 (bs, 1H), 7.49 (d, J=8.4 Hz, 1H), 6.23 (d, J=8.4 Hz, 1H).

References:

Arromax Pharmatech Co., Ltd.;HONG, Jian;XU, Xin;LE, Xiaoyong;ZHANG, Zonghua EP3181553, 2017, A1 Location in patent:Paragraph 0278; 0279

471-25-0
234 suppliers
$10.00/1g

1609-93-4
49 suppliers
$40.00/100mg

References