(E)-3-(2,6,6-trimethylcyclohex-1-en-1-yl)acryloyl chloride

Base Information

• Chemical Name: (E)-3-(2,6,6-trimethylcyclohex-1-en-1-yl)acryloyl chloride
• CAS No.: 69258-08-8
• Molecular Formula: C₁₂H₁₇ClO
• Molecular Weight: 212.719
• Mol file: 69258-08-8.mol

Synonyms:(E)-3-(2,6,6-trimethylcyclohex-1-en-1-yl)acryloyl chloride

Chemical Property of (E)-3-(2,6,6-trimethylcyclohex-1-en-1-yl)acryloyl chloride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-3-(2,6,6-trimethylcyclohex-1-en-1-yl)acryloyl chloride

There total 3 articles about (E)-3-(2,6,6-trimethylcyclohex-1-en-1-yl)acryloyl 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:

3-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-propenoic acid (37384-69-3) + (E)-3-(2,6,6-trimethylcyclohex-1-enyl)acrylic acid (14393-45-4) → (E)-3-(2,6,6-trimethylcyclohex-1-en-1-yl)acryloyl chloride (69258-08-8) + α-Cyclocitrylideneacetyl chloride

Guidance literature:

With oxalyl dichloride; N,N-dimethyl-formamide; In tetrahydrofuran; at 20 ℃; for 3h;

Reference yield:

(E)-β-ionone (79-77-6,14901-07-6) → (E)-3-(2,6,6-trimethylcyclohex-1-en-1-yl)acryloyl chloride (69258-08-8)

Guidance literature:

Multi-step reaction with 2 steps

1: bromine; sodium hydroxide / water; 1,4-dioxane / 4 h / 20 °C

2: thionyl chloride / 1.3 h / 50 °C

With thionyl chloride; bromine; sodium hydroxide; In 1,4-dioxane; water;

DOI:10.1007/s00280-017-3265-1

Reference yield:

(E)-3-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-propensaeure-ethylester (80922-54-9) → (E)-3-(2,6,6-trimethylcyclohex-1-en-1-yl)acryloyl chloride (69258-08-8)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide / ethanol; water / 4 h / 40 °C

2: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

With oxalyl dichloride; N,N-dimethyl-formamide; sodium hydroxide; In ethanol; dichloromethane; water;

DOI:10.1021/acs.orglett.9b03842

upstream raw materials:

3-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-propenoic acid

(E)-3-(2,6,6-trimethylcyclohex-1-enyl)acrylic acid

(E)-β-ionone

(E)-3-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-propensaeure-ethylester

Downstream raw materials:

methyl (Z)-3-(2,6,6-trimethylcyclohex-1-en-1-yl)acrylate

Refernces

• 1、 Livingstone, Keith,Tenberge, Marius,Pape, Felix,Daniliuc, Constantin G.,Jamieson, Craig,Gilmour, Ryan. "Photocatalytic e → Z Isomerization of β-Ionyl Derivatives". . p. 9677 - 9680. Retrieved 2019/11/29.
• 2、 -. "ANTINEOPLASTIC AND CURCUMIN DERIVATIVES AND METHODS OF PREPARATION AND USE". Page/Page column 10-11. . Retrieved 2010/11/28.