(E)-3-(3-Benzyloxymethoxy-phenyl)-acrylic acid ethyl ester

Base Information

• Chemical Name: (E)-3-(3-Benzyloxymethoxy-phenyl)-acrylic acid ethyl ester
• CAS No.: 155433-47-9
• Molecular Formula: C₁₉H₂₀O₄
• Molecular Weight: 312.365
• Mol file: 155433-47-9.mol

Synonyms:(E)-3-(3-Benzyloxymethoxy-phenyl)-acrylic acid ethyl ester

Chemical Property of (E)-3-(3-Benzyloxymethoxy-phenyl)-acrylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-3-(3-Benzyloxymethoxy-phenyl)-acrylic acid ethyl ester

There total 1 articles about (E)-3-(3-Benzyloxymethoxy-phenyl)-acrylic acid ethyl 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:

Benzyloxymethyl chloride (3587-60-8) + 3-hydroxy-trans-cinnamic acid (14755-02-3,588-30-7) → (E)-3-(3-Benzyloxymethoxy-phenyl)-acrylic acid ethyl ester (155433-47-9)

Guidance literature:

DOI:10.1016/S0040-4020(01)81547-7

Reference yield: 92.0%

(E)-3-(3-Benzyloxymethoxy-phenyl)-acrylic acid ethyl ester (155433-47-9) → m-benzyloxymethoxycinnamyl alcohol (137531-98-7)

Guidance literature:

With diisobutylaluminium hydride; In hexane; dichloromethane; at -78 ℃; for 1h;

DOI:10.1016/S0040-4020(01)81547-7

Reference yield:

(E)-3-(3-Benzyloxymethoxy-phenyl)-acrylic acid ethyl ester (155433-47-9) → (2R,3R,4R,5S,8S)-8--1,2-epoxy-8-methoxy-4-(p-methoxybenzyloxy)-3,5-dimethyloctane (110314-58-4)

Guidance literature:

Multi-step reaction with 15 steps

1: 92 percent / diisobutyl aluminum hydride / CH₂Cl₂; hexane / 1 h / -78 °C

2: 90 percent / (-)-diisopropyl tartrate, titanium tetraisopropoxide, t-butyl hydroperoxide, MS 4 Angstroem / CH₂Cl₂; toluene / 11 h / -20 °C

3: 91 percent / Red-al / toluene; tetrahydrofuran / 10.2 h / 0 °C

4: 93 percent / triethylamine, 4-DMAP / CH₂Cl₂ / 4 h / Ambient temperature

5: sodium hydride / tetrahydrofuran; dimethylformamide / 5 h / Ambient temperature

6: sodium bromide / dimethylformamide / 48 h / Ambient temperature

7: Mg / tetrahydrofuran / 1 h / Irradiation

8: CuI / tetrahydrofuran

9: 93 percent / 4-dimethylaminopyridine / tetrahydrofuran / 12 h / Ambient temperature

10: 62 percent / lithium aluminum hydride / tetrahydrofuran / 14 h / Ambient temperature

11: 91 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 12 h / Ambient temperature

12: 86 percent / PPTS / methanol / 36 h / Ambient temperature

13: 97 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 12 h / Ambient temperature

14: 31 percent / aq. KOH; methanol / 24 h / Ambient temperature

15: 87 percent / NaH / tetrahydrofuran; dimethylformamide / 24 h / Ambient temperature

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; lithium aluminium tetrahydride; (-)-diisopropyl tartrate; MS 4 Angstroem; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; magnesium; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; sodium bromide; copper(l) iodide; In tetrahydrofuran; methanol; potassium hydroxide; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4020(01)81547-7

upstream raw materials:

Benzyloxymethyl chloride

3-hydroxy-trans-cinnamic acid

Downstream raw materials:

m-benzyloxymethoxycinnamyl alcohol

(S)-3-(m-benzyloxymethoxyphenyl)propane-1,3-diol

(S)-3-(m-benzyloxymethoxyphenyl)-1-bromo-3-methoxypropane

(2R,3R,4R,5S,8S)-8-(m-benzyloxymethylphenyl)-1,2-epoxy-8-methoxy-3,5-dimethyloctan-4-ol