3-(4-(Benzyloxy)-3-methoxyphenyl)propanoic acid

Base Information

• Chemical Name: 3-(4-(Benzyloxy)-3-methoxyphenyl)propanoic acid
• CAS No.: 30034-49-2
• Molecular Formula: C17H18O4
• Molecular Weight: 286.328
• Hs Code.: 2918990090
• DSSTox Substance ID: DTXSID90372900
• Nikkaji Number: J1.944.954H
• Wikidata: Q82160860
• Mol file: 30034-49-2.mol

Synonyms:30034-49-2;3-Methoxy-4-(benzyloxy)-benzenepropanoic acid;3-(4-(benzyloxy)-3-methoxyphenyl)propanoic acid;3-(3-methoxy-4-phenylmethoxyphenyl)propanoic acid;3-Methoxy-4-(benzyloxy)benzenepropanoic acid;3-(3-methoxy-4-benzyloxyphenyl)propionic acid;3-[4-(benzyloxy)-3-methoxyphenyl]propanoic acid;SCHEMBL5209587;DTXSID90372900;SJEFIQLTGBLFBB-UHFFFAOYSA-N;MFCD00185555;AKOS002674127;AS-66739;3-Methoxy-4-(benzyloxy)-benzenepropanoicacid;3-Methoxy-4-(benzyloxy)benzenepropionic acid;CS-0061928;W17515;3-(4-benzyloxy-3-methoxy-phenyl)-propionic acid

Chemical Property of 3-(4-(Benzyloxy)-3-methoxyphenyl)propanoic acid

Chemical Property:

• PSA: 55.76000
• LogP: 3.29140
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 286.12050905
• Heavy Atom Count: 21
• Complexity: 312

Purity/Quality:

99% ^*data from raw suppliers

3-Methoxy-4-(benzyloxy)-benzenepropanoicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)CCC(=O)O)OCC2=CC=CC=C2

Technology Process of 3-(4-(Benzyloxy)-3-methoxyphenyl)propanoic acid

There total 11 articles about 3-(4-(Benzyloxy)-3-methoxyphenyl)propanoic 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: 93.0%

ethyl 3-(4-(benzyloxy)-3-methoxy)propanoate (186895-24-9) → β-(4-benzyloxy-3-methoxyphenyl)propionic acid (30034-49-2)

Guidance literature:

ethyl 3-(4-(benzyloxy)-3-methoxy)propanoate; With sodium hydroxide; water; at 20 ℃; for 2h;

With hydrogenchloride; In water;

Reference yield: 85.0%

benzyl 3-[4-(benzyloxy)-3-methoxyphenyl]propanoate (116185-11-6) → β-(4-benzyloxy-3-methoxyphenyl)propionic acid (30034-49-2)

Guidance literature:

With methanol; water; potassium hydroxide; In tetrahydrofuran; at 20 - 60 ℃; for 4h;

DOI:10.1016/j.tetlet.2019.151360

Reference yield:

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6,537-98-4) → β-(4-benzyloxy-3-methoxyphenyl)propionic acid (30034-49-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / H₂ / Pd/C / ethyl acetate; methanol / 5 h / 2068.59 Torr

2: K₂CO₃ / acetone; acetonitrile / 15 h / Heating

3: 1.26 g / KOH / methanol; H₂O / 10 h / 70 °C

With potassium hydroxide; hydrogen; potassium carbonate; palladium on activated charcoal; In methanol; water; ethyl acetate; acetone; acetonitrile;

DOI:10.1016/S0968-0896(03)00394-8

upstream raw materials:

3-(4-benzyloxy-3-methoxy-phenyl)-propionitrile

4-benzyloxy-3-methoxycinnamic acid

3-(4-hydroxy-3-methoxyphenyl)propionic acid

benzyl chloride

Downstream raw materials:

(S)-3-[(S)-2-(4-benzyloxy-3-methoxybenzyl)pent-4-enoyl]-4-isopropyloxazolidin-2-one

(S)-2-(4-benzyloxy-3-methoxybenzyl)pent-4-en-1-ol

(R)-4-benzyl-3-[3-(4-benzyloxy-3-methoxyphenyl)propanoyl]oxazolidin-2-one

(R)-4-benzyl-3-[(R)-2-(4-benzyloxy-3-methoxybenzyl)pent-4-enoyl]oxazolidin-2-one

Refernces

• 1、 Nishimura, Katsumi,Horii, Shinji,Tanahashi, Takao. "Asymmetric synthesis of O-methylneferine". . p. 865 - 876. Retrieved 2019/04/26.
• 2、 Allais, Florent,Pla, Thomas J. L.,Ducrot, Paul-Henri. "An access to chiral β-benzyl-γ-butyrolactones and its application to the synthesis of enantiopure (+)-secoisolariciresinol, (-)-secoisolariciresinol, and (-)-enterolactone". experimental part. p. 1456 - 1464. Retrieved 2011/06/17.