Toluene-4-sulfonic acid (E)-(S)-3-(4-methoxy-phenyl)-2-methyl-hex-4-enyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (E)-(S)-3-(4-methoxy-phenyl)-2-methyl-hex-4-enyl ester
• CAS No.: 1027314-32-4
• Molecular Formula: C₂₁H₂₆O₄S
• Molecular Weight: 374.501
• Mol file: 1027314-32-4.mol

Synonyms:

Chemical Property of Toluene-4-sulfonic acid (E)-(S)-3-(4-methoxy-phenyl)-2-methyl-hex-4-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (E)-(S)-3-(4-methoxy-phenyl)-2-methyl-hex-4-enyl ester

There total 6 articles about Toluene-4-sulfonic acid (E)-(S)-3-(4-methoxy-phenyl)-2-methyl-hex-4-enyl ester 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:

(E)-1-(4-methoxyphenyl)pent-1-en-3-ol (32271-54-8,134747-45-8,77254-94-5) → Toluene-4-sulfonic acid (E)-(S)-3-(4-methoxy-phenyl)-2-methyl-hex-4-enyl ester (1027314-32-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 46 percent / Burkholderia cepacia lipase / various solvent(s) / 15 h / 20 °C

2.1: 95 percent / KOH / ethanol; H₂O / 5 h / Heating

3.1: propionic acid / 7 h / 150 - 155 °C

3.2: 77 percent / KOH / ethanol; H₂O / 6 h / Heating

4.1: LiAlH₄ / tetrahydrofuran / 0.5 h / Heating

5.1: pyridine / 16 h

With pyridine; Burkholderia cepacia lipase; potassium hydroxide; lithium aluminium tetrahydride; propionic acid; In tetrahydrofuran; ethanol; water; 3.1: Claisen-Johnson rearrangement;

DOI:10.1016/j.tetasy.2003.11.021

Reference yield:

(+)-(2R,3E)-4-(4'-methoxyphenyl)but-3-en-2-ol (174174-00-6) → Toluene-4-sulfonic acid (E)-(S)-3-(4-methoxy-phenyl)-2-methyl-hex-4-enyl ester (1027314-32-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: propionic acid / 7 h / 150 - 155 °C

1.2: 77 percent / KOH / ethanol; H₂O / 6 h / Heating

2.1: LiAlH₄ / tetrahydrofuran / 0.5 h / Heating

3.1: pyridine / 16 h

With pyridine; lithium aluminium tetrahydride; propionic acid; In tetrahydrofuran; 1.1: Claisen-Johnson rearrangement;

DOI:10.1016/j.tetasy.2003.11.021

Reference yield:

4-(4-methoxyphenyl)-3-buten-2-one (3815-30-3) → Toluene-4-sulfonic acid (E)-(S)-3-(4-methoxy-phenyl)-2-methyl-hex-4-enyl ester (1027314-32-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 88 percent / NaBH₄ / methanol / 0.5 h / Heating

2.1: 46 percent / Burkholderia cepacia lipase / various solvent(s) / 15 h / 20 °C

3.1: 95 percent / KOH / ethanol; H₂O / 5 h / Heating

4.1: propionic acid / 7 h / 150 - 155 °C

4.2: 77 percent / KOH / ethanol; H₂O / 6 h / Heating

5.1: LiAlH₄ / tetrahydrofuran / 0.5 h / Heating

6.1: pyridine / 16 h

With pyridine; Burkholderia cepacia lipase; potassium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; propionic acid; In tetrahydrofuran; methanol; ethanol; water; 4.1: Claisen-Johnson rearrangement;

DOI:10.1016/j.tetasy.2003.11.021

upstream raw materials:

p-toluenesulfonyl chloride

(E)-1-(4-methoxyphenyl)pent-1-en-3-ol

(+)-(2R,3E)-4-(4'-methoxyphenyl)but-3-en-2-ol

4-(4-methoxyphenyl)-3-buten-2-one

Downstream raw materials:

(S)-1-[1-(bromomethyl)-2-methylpropyl]-4-methoxybenzene

(2S)-2-(4-methoxyphenyl)-3-methylbutan-1-ol

(S)-4-(4-methoxyphenyl)-5-methylhexanoic acid