(3-Hydroxy-4-methoxy-2,6-dimethyl-phenyl)-acetic acid (E)-2-(3-hydroxy-4-methoxy-2,6-dimethyl-phenyl)-vinyl ester

Base Information

Chemical Name:(3-Hydroxy-4-methoxy-2,6-dimethyl-phenyl)-acetic acid (E)-2-(3-hydroxy-4-methoxy-2,6-dimethyl-phenyl)-vinyl ester
CAS No.:80367-41-5
Molecular Formula:C₂₂H₂₆O₆
Molecular Weight:386.445
Hs Code.:

Synonyms:(3-Hydroxy-4-methoxy-2,6-dimethyl-phenyl)-acetic acid (E)-2-(3-hydroxy-4-methoxy-2,6-dimethyl-phenyl)-vinyl ester

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Chemical Property of (3-Hydroxy-4-methoxy-2,6-dimethyl-phenyl)-acetic acid (E)-2-(3-hydroxy-4-methoxy-2,6-dimethyl-phenyl)-vinyl ester

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Technology Process of (3-Hydroxy-4-methoxy-2,6-dimethyl-phenyl)-acetic acid (E)-2-(3-hydroxy-4-methoxy-2,6-dimethyl-phenyl)-vinyl ester

There total 9 articles about (3-Hydroxy-4-methoxy-2,6-dimethyl-phenyl)-acetic acid (E)-2-(3-hydroxy-4-methoxy-2,6-dimethyl-phenyl)-vinyl 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:

: 1131-94-8
homoisovanillic acid

: 80367-41-5
(3-Hydroxy-4-methoxy-2,6-dimethyl-phenyl)-acetic acid (E)-2-(3-hydroxy-4-methoxy-2,6-dimethyl-phenyl)-vinyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 100 percent / KOH / ethanol / 12 h / Heating

2: HCl, H₂ / 10percent Pd/C / ethanol / 8 h / 125 °C / 129287 Torr

3: H₂SO₄ / 6 h / Heating

4: 1.) K₂CO₃ / 1.) acetone, reflux, 30 min, 2.) reflux, 14 h

5: 98 percent / Diisobutylaluminum Hydride / diethyl ether; hexane / 0.5 h / -78 °C

6: 1.) lithium tetramethylpiperidide / 1.) THF, room temperature, 45 min, 2.) reflux, 3 h

7: 1.) trimethylsilyl iodide, triethylamine, 2.) CH₃OH / 1.) CH₃CN, 35-40 deg C, 2 h, 2.) reflux

With hydrogenchloride; methanol; potassium hydroxide; trimethylsilyl iodide; sulfuric acid; 2,2,6,6-tetramethylpiperidinyl-lithium; hydrogen; diisobutylaluminium hydride; potassium carbonate; triethylamine; palladium on activated charcoal; In diethyl ether; ethanol; hexane;
DOI:10.1021/jo00343a003

Reference yield:

: 80367-35-7
(3-Hydroxy-4-methoxy-2,6-bis-morpholin-4-ylmethyl-phenyl)-acetic acid

: 80367-41-5
(3-Hydroxy-4-methoxy-2,6-dimethyl-phenyl)-acetic acid (E)-2-(3-hydroxy-4-methoxy-2,6-dimethyl-phenyl)-vinyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: HCl, H₂ / 10percent Pd/C / ethanol / 8 h / 125 °C / 129287 Torr

2: H₂SO₄ / 6 h / Heating

3: 1.) K₂CO₃ / 1.) acetone, reflux, 30 min, 2.) reflux, 14 h

4: 98 percent / Diisobutylaluminum Hydride / diethyl ether; hexane / 0.5 h / -78 °C

5: 1.) lithium tetramethylpiperidide / 1.) THF, room temperature, 45 min, 2.) reflux, 3 h

6: 1.) trimethylsilyl iodide, triethylamine, 2.) CH₃OH / 1.) CH₃CN, 35-40 deg C, 2 h, 2.) reflux

With hydrogenchloride; methanol; trimethylsilyl iodide; sulfuric acid; 2,2,6,6-tetramethylpiperidinyl-lithium; hydrogen; diisobutylaluminium hydride; potassium carbonate; triethylamine; palladium on activated charcoal; In diethyl ether; ethanol; hexane;
DOI:10.1021/jo00343a003

Reference yield:

: 80367-46-0
(3-Hydroxy-4-methoxy-2,6-dimethyl-phenyl)-acetic acid

: 80367-41-5
(3-Hydroxy-4-methoxy-2,6-dimethyl-phenyl)-acetic acid (E)-2-(3-hydroxy-4-methoxy-2,6-dimethyl-phenyl)-vinyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: H₂SO₄ / 6 h / Heating

2: 1.) K₂CO₃ / 1.) acetone, reflux, 30 min, 2.) reflux, 14 h

3: 98 percent / Diisobutylaluminum Hydride / diethyl ether; hexane / 0.5 h / -78 °C

4: 1.) lithium tetramethylpiperidide / 1.) THF, room temperature, 45 min, 2.) reflux, 3 h

5: 1.) trimethylsilyl iodide, triethylamine, 2.) CH₃OH / 1.) CH₃CN, 35-40 deg C, 2 h, 2.) reflux

With methanol; trimethylsilyl iodide; sulfuric acid; 2,2,6,6-tetramethylpiperidinyl-lithium; diisobutylaluminium hydride; potassium carbonate; triethylamine; In diethyl ether; hexane;
DOI:10.1021/jo00343a003