p-acetoxycinnamoyl chloride

Base Information

• Chemical Name: p-acetoxycinnamoyl chloride
• CAS No.: 53901-95-4
• Molecular Formula: C₁₁H₉ClO₃
• Molecular Weight: 224.644
• Mol file: 53901-95-4.mol

Synonyms:

Chemical Property of p-acetoxycinnamoyl chloride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-acetoxycinnamoyl chloride

There total 9 articles about p-acetoxycinnamoyl chloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

4-acetoxycinnamic acid (27542-85-4) → p-acetoxycinnamoyl chloride (53901-95-4,108608-06-6,58523-18-5)

Guidance literature:

With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2009.08.047

Reference yield:

p-Coumaric Acid (7400-08-0,50940-26-6) + acetic anhydride (108-24-7) → p-acetoxycinnamoyl chloride (53901-95-4,108608-06-6,58523-18-5)

Guidance literature:

p-Coumaric Acid; acetic anhydride; at 140 ℃; for 4h;

With thionyl chloride; In acetonitrile; at 80 ℃; for 6h;

Reference yield:

p-Coumaric Acid (7400-08-0,50940-26-6) → p-acetoxycinnamoyl chloride (53901-95-4,108608-06-6,58523-18-5)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine; 4-(dimethylamino)pyridine / 1 h / 0 °C

2: SOCl₂ / Heating

With pyridine; dmap; thionyl chloride;

DOI:10.1021/jf053207q

upstream raw materials:

3-(4-acetoxyphenyl)acrylic acid

4-acetoxycinnamic acid

p-Coumaric Acid

4-formylphenyl acetate

Downstream raw materials:

1-(4-Acetoxyphenyl)-7-methoxy-hepta-1,6-dien-4-in-3-on

6α-O-acetyl-p-coumaroyloxy-5,7αH-eudesm-3-ene

(E)-3-(4-Acetoxy-phenyl)-acrylic acid (1S,2S)-2-[(E)-3-(4-acetoxy-phenyl)-acryloyloxy]-cyclohexyl ester

(E)-3-(4-Acetoxy-phenyl)-acrylic acid (1R,2R)-2-[(E)-3-(4-acetoxy-phenyl)-acryloyloxy]-cyclohexyl ester

Refernces

• 1、 -. "Preparation method and application of hydroxyl cinnamyl ester type catechin". Paragraph 0065; 0071; 0091. . Retrieved 2020/06/24.
• 2、 Zhao, Tingxing,Qin, Dekun,Han, Weiguo,Yang, Shiping,Feng, Boya,Gao, Ge,You, Jingsong. "Co(iii)-catalyzed: Z -selective oxidative C-H/C-H cross-coupling of alkenes with triisopropylsilylacetylene". supporting information. p. 6118 - 6121. Retrieved 2019/06/03.