(E)-4-<2',6',6'-trimethylcyclohex-2'-enyl>but-3-en-2-one ethylene ketal

Base Information

• Chemical Name: (E)-4-<2',6',6'-trimethylcyclohex-2'-enyl>but-3-en-2-one ethylene ketal
• CAS No.: 14398-37-9
• Molecular Formula: C₁₅H₂₄O₂
• Molecular Weight: 236.354
• Mol file: 14398-37-9.mol

Synonyms:(E)-4-<2',6',6'-trimethylcyclohex-2'-enyl>but-3-en-2-one ethylene ketal

Chemical Property of (E)-4-<2',6',6'-trimethylcyclohex-2'-enyl>but-3-en-2-one ethylene ketal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-4-<2',6',6'-trimethylcyclohex-2'-enyl>but-3-en-2-one ethylene ketal

There total 1 articles about (E)-4-<2',6',6'-trimethylcyclohex-2'-enyl>but-3-en-2-one ethylene ketal 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:

alpha-ionone (127-41-3,6901-97-9,14398-36-8,24190-29-2,30685-95-1,31798-12-6,52340-45-1,67529-94-6,67529-95-7) + ethylene glycol (107-21-1) → (E)-4-<2',6',6'-trimethylcyclohex-2'-enyl>but-3-en-2-one ethylene ketal (14398-37-9)

Guidance literature:

With toluene-4-sulfonic acid; trimethyl orthoformate; In hexane; at 20 ℃; Inert atmosphere;

DOI:10.1055/s-0030-1258382

Reference yield:

(E)-4-<2',6',6'-trimethylcyclohex-2'-enyl>but-3-en-2-one ethylene ketal (14398-37-9) → (3R)-cryptoxanthin (472-70-8)

Guidance literature:

Multi-step reaction with 8 steps

1.1: potassium carbonate; tert.-butylhydroperoxide; sodium hypochlorite / acetonitrile; water / 9.5 h / -5 - 0 °C / Inert atmosphere; Cooling with ice-salt

2.1: sodium tetrahydroborate / ethanol / 4 h / 10 - 20 °C

3.1: hydrogenchloride / water; acetone / 3.16 h / 20 °C / Inert atmosphere

4.1: immobilized lipase PS (pseudomonas cepacia) / ethyl acetate / 20 °C / Inert atmosphere

5.1: potassium hydroxide / dichloromethane; methanol / 2 h / 0 °C / Inert atmosphere

5.2: pH 5

6.1: toluene / 1.5 h / -20 °C / Inert atmosphere

7.1: methanol / 0 - 20 °C

8.1: ethyloxirane / ethanol / Reflux; Inert atmosphere

With ethyloxirane; hydrogenchloride; tert.-butylhydroperoxide; sodium hypochlorite; sodium tetrahydroborate; potassium carbonate; potassium hydroxide; immobilized lipase PS (pseudomonas cepacia); In methanol; ethanol; dichloromethane; water; ethyl acetate; acetone; toluene; acetonitrile; 7.1: Wittig Reaction;

Reference yield:

(E)-4-<2',6',6'-trimethylcyclohex-2'-enyl>but-3-en-2-one ethylene ketal (14398-37-9) → zeaxanthin (144-68-3,3309-19-1,24502-92-9,29472-68-2,31272-50-1,31272-53-4,57820-80-1,60046-54-0,60497-64-5,60497-65-6,72002-36-9,72580-10-0,100347-92-0,100347-97-5,136656-95-6,136733-98-7,136733-99-8,136734-01-5,136734-02-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: potassium carbonate; tert.-butylhydroperoxide; sodium hypochlorite / acetonitrile; water / 9.5 h / -5 - 0 °C / Inert atmosphere; Cooling with ice-salt

2.1: sodium tetrahydroborate / ethanol / 4 h / 10 - 20 °C

3.1: hydrogenchloride / water; acetone / 3.16 h / 20 °C / Inert atmosphere

4.1: immobilized lipase PS (pseudomonas cepacia) / ethyl acetate / 20 °C / Inert atmosphere

5.1: potassium hydroxide / dichloromethane; methanol / 2 h / 0 °C / Inert atmosphere

5.2: pH 5

6.1: toluene / 1.5 h / -20 °C / Inert atmosphere

7.1: methanol / 0 - 20 °C

8.1: ethanol / 22 h / Reflux; Inert atmosphere

With hydrogenchloride; tert.-butylhydroperoxide; sodium hypochlorite; sodium tetrahydroborate; potassium carbonate; potassium hydroxide; immobilized lipase PS (pseudomonas cepacia); In methanol; ethanol; dichloromethane; water; ethyl acetate; acetone; toluene; acetonitrile; 7.1: Wittig Reaction;

upstream raw materials:

alpha-ionone

ethylene glycol

Downstream raw materials:

(R)-α-ionone

(3E)-4-[(S)-2,6,6-trimethylcyclohex-2-enyl]but-3-en-2-one

zeaxanthin

(3R)-cryptoxanthin