2-isopropyl-3-{2-[3-methoxy(propyloxy)]-4-methoxyphenyl}propionic acid

Base Information

• Chemical Name: 2-isopropyl-3-{2-[3-methoxy(propyloxy)]-4-methoxyphenyl}propionic acid
• CAS No.: 325154-22-1
• Molecular Formula: C₁₇H₂₆O₅
• Molecular Weight: 310.39
• Mol file: 325154-22-1.mol

Synonyms:2-isopropyl-3-{2-[3-methoxy(propyloxy)]-4-methoxyphenyl}propionic acid

Chemical Property of 2-isopropyl-3-{2-[3-methoxy(propyloxy)]-4-methoxyphenyl}propionic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of 2-isopropyl-3-{2-[3-methoxy(propyloxy)]-4-methoxyphenyl}propionic acid

There total 11 articles about 2-isopropyl-3-{2-[3-methoxy(propyloxy)]-4-methoxyphenyl}propionic acid 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:

4-methoxy-3-(3-methoxypropoxy)benzaldehyde (172900-75-3) → 2-isopropyl-3-{2-[3-methoxy(propyloxy)]-4-methoxyphenyl}propionic acid (325154-22-1)

Guidance literature:

Multi-step reaction with 4 steps

1: lithium diisopropyl amide / -40 °C / Inert atmosphere

2: camphor-10-sulfonic acid / toluene / Inert atmosphere

3: hydrogen; palladium on activated charcoal / methanol / Inert atmosphere

4: sodium hydroxide; water / ethanol / Reflux; Inert atmosphere

With palladium on activated charcoal; camphor-10-sulfonic acid; water; hydrogen; sodium hydroxide; lithium diisopropyl amide; In methanol; ethanol; toluene; 1: |Aldol Addition;

DOI:10.1021/acs.oprd.5b00396

Reference yield:

dimethyl-2(4-methoxy-3-(3-methoxypropyloxy)-benzyl)-2-isopropyl malonate (1381757-31-8) → 2-isopropyl-3-{2-[3-methoxy(propyloxy)]-4-methoxyphenyl}propionic acid (325154-22-1)

Guidance literature:

dimethyl-2(4-methoxy-3-(3-methoxypropyloxy)-benzyl)-2-isopropyl malonate; With water; sodium hydroxide; In ethanol; for 72h; Reflux;

With hydrogenchloride; In ethanol; water; pH=1 - 1.2;

With sodium hydroxide; In water; dimethyl sulfoxide; at 155 ℃; for 35h;

Reference yield:

C21H32O5 → 2-isopropyl-3-{2-[3-methoxy(propyloxy)]-4-methoxyphenyl}propionic acid (325154-22-1) + C21H34O5 + C21H34O5

Guidance literature:

With C₃₇H₄₀IrNOP⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-); hydrogen; In dichloromethane; at 20 ℃; for 2h; under 37503.8 Torr; Overall yield = 100 %Chromat.; Optical yield = 57 %ee; enantioselective reaction; Autoclave;

DOI:10.1002/anie.201301251

upstream raw materials:

3-hydroxy-4-methoxybenzyl alcohol

4-(bromomethyl)-1-methoxy-2-(3-methoxypropoxy)-benzene

[4-methoxy-3-(3-methoxypropoxy)-phenyl]methanol

dimethyl-2(4-methoxy-3-(3-methoxypropyloxy)-benzyl)-2-isopropyl malonate

Downstream raw materials:

(R)-2-[4-methoxy-3-(3-methoxypropoxy)benzyl]-3-methylbutanol

(R)-3-[4-methoxy-3-(3-methoxypropoxy)phenyl]-2-(1-methylethyl)propanoic acid

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

butyl-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutanoate

Refernces

• 1、 Schumacher, Andreas,Bernasconi, Maurizio,Pfaltz, Andreas. "Chiral N-heterocyclic carbene/pyridine ligands for the iridium-catalyzed asymmetric hydrogenation of olefins". supporting information. p. 7422 - 7425. Retrieved 2013/07/26.