toluene-4-sulfonic acid 4-[(1E)-3-hydroxy-1-propenyl]phenyl ester

Base Information

• Chemical Name: toluene-4-sulfonic acid 4-[(1E)-3-hydroxy-1-propenyl]phenyl ester
• CAS No.: 944249-85-8
• Molecular Formula: C₁₆H₁₆O₄S
• Molecular Weight: 304.367
• Mol file: 944249-85-8.mol

Synonyms:toluene-4-sulfonic acid 4-[(1E)-3-hydroxy-1-propenyl]phenyl ester

Chemical Property of toluene-4-sulfonic acid 4-[(1E)-3-hydroxy-1-propenyl]phenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of toluene-4-sulfonic acid 4-[(1E)-3-hydroxy-1-propenyl]phenyl ester

There total 4 articles about toluene-4-sulfonic acid 4-[(1E)-3-hydroxy-1-propenyl]phenyl 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: 96.0%

(2E)-3-[4-(toluene-4-sulfonyloxy)phenyl]-2-propenoic acid ethyl ester (944249-84-7) → toluene-4-sulfonic acid 4-[(1E)-3-hydroxy-1-propenyl]phenyl ester (944249-85-8)

Guidance literature:

With diisobutylaluminium hydride; In hexane; dichloromethane; at -78 ℃;

DOI:10.1021/jacs.7b05619

Reference yield:

4-tosyloxybenzaldehyde (80459-48-9) → toluene-4-sulfonic acid 4-[(1E)-3-hydroxy-1-propenyl]phenyl ester (944249-85-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / Et₃N; LiBr / tetrahydrofuran / 4 h / 20 °C

2: 95 percent / DIBAL-H / tetrahydrofuran; hexane / 2 h / 0 °C

With diisobutylaluminium hydride; triethylamine; lithium bromide; In tetrahydrofuran; hexane; 1: Horner-Emmons-Wadsworth olefination;

DOI:10.1039/b704211f

Reference yield:

4-hydroxy-benzaldehyde (123-08-0,65581-83-1) → toluene-4-sulfonic acid 4-[(1E)-3-hydroxy-1-propenyl]phenyl ester (944249-85-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triethylamine / dichloromethane / 0.17 h / 0 °C

1.2: 5 h / 0 - 20 °C

2.1: dichloromethane / 16 h / 20 °C

3.1: diisobutylaluminium hydride / hexane; dichloromethane / -78 °C

With diisobutylaluminium hydride; triethylamine; In hexane; dichloromethane;

DOI:10.1021/jacs.7b05619

upstream raw materials:

(2E)-3-[4-(toluene-4-sulfonyloxy)phenyl]-2-propenoic acid ethyl ester

4-tosyloxybenzaldehyde

4-hydroxy-benzaldehyde

p-toluenesulfonyl chloride

Downstream raw materials:

toluene-4-sulfonic acid 4-[(2S,3R)-3-hydroxymethyloxyranyl]phenyl ester

(E)-4-(3-((diethoxyphosphoryl)oxy)prop-1-en-1-yl)phenyl 4-methylbenzene sulfonate

4-{(2R,3R)-3-methyl-5-[(E)prop-1-en-1-yl]-2,3-dihydrobenzofuran-2-yl}phenol

(S)-1-phenyl-1-propanol