2-Benzyloxymethyl-4-methyl-furan-3-carboxylic acid

Base Information

• Chemical Name: 2-Benzyloxymethyl-4-methyl-furan-3-carboxylic acid
• CAS No.: 142041-30-3
• Molecular Formula: C₁₄H₁₄O₄
• Molecular Weight: 246.263
• Mol file: 142041-30-3.mol

Synonyms:

Chemical Property of 2-Benzyloxymethyl-4-methyl-furan-3-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Benzyloxymethyl-4-methyl-furan-3-carboxylic acid

There total 1 articles about 2-Benzyloxymethyl-4-methyl-furan-3-carboxylic 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:

methyl 4-methyl-2-<(phenylmethoxy)methyl>-3-furancarboxylate (142041-29-0) → 2-Benzyloxymethyl-4-methyl-furan-3-carboxylic acid (142041-30-3)

Guidance literature:

With lithium hydroxide; In methanol; for 72h; Ambient temperature;

DOI:10.1021/jo00042a036

Reference yield:

2-Benzyloxymethyl-4-methyl-furan-3-carboxylic acid (142041-30-3) → 5-methyl-1-<(phenylmethoxy)methyl>-7-oxabicyclo<2.2.1>hept-5-en-2-one (142041-34-7)

Guidance literature:

Multi-step reaction with 3 steps

1: copper-bronze, quinoline / 1 h / Heating

2: 98 percent / hydroquinone / CH₂Cl₂ / 312 h / 9050090 Torr

3: 1) 1 M aq. KOH, 2) 37percent aq. formaldehyde / 1) THF, water, r.t., 45 min, 2) 20 min

With quinoline; potassium hydroxide; formaldehyd; copper; hydroquinone; In dichloromethane;

DOI:10.1021/jo00042a036

Reference yield:

2-Benzyloxymethyl-4-methyl-furan-3-carboxylic acid (142041-30-3) → (2-exo,3-endo,6-endo)-6-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-3-methyl-1-<(phenylmethoxy)methyl>-7-oxabicyclo<2.2.1>heptan-2-ol (142041-36-9)

Guidance literature:

Multi-step reaction with 6 steps

1: copper-bronze, quinoline / 1 h / Heating

2: 98 percent / hydroquinone / CH₂Cl₂ / 312 h / 9050090 Torr

3: 1) 1 M aq. KOH, 2) 37percent aq. formaldehyde / 1) THF, water, r.t., 45 min, 2) 20 min

4: 95 percent / diisobutylaluminum hydride / tetrahydrofuran; hexane / 1.5 h / -78 °C

5: 96 percent / imidazole / dimethylformamide / 16 h / Ambient temperature

6: 1) borane-THF complex, 2) 5 M aq. NaOH, 30percent H₂O₂ / 1) THF, 0 deg C, 1 h, then r.t., 1 h, 2) reflux, 30 min

With 1H-imidazole; quinoline; potassium hydroxide; sodium hydroxide; formaldehyd; borane-THF; dihydrogen peroxide; copper; diisobutylaluminium hydride; hydroquinone; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00042a036

upstream raw materials:

methyl 4-methyl-2-<(phenylmethoxy)methyl>-3-furancarboxylate

Downstream raw materials:

4-methyl-2-<(phenylmethoxy)methyl>furan

endo-5-methyl-1-<(phenylmethoxy)methyl>-7-oxabicyclo<2.2.1>hept-5-en-2-ol

5-methyl-1-<(phenylmethoxy)methyl>-7-oxabicyclo<2.2.1>hept-5-en-2-one

(2-exo,3-endo,6-endo)-6-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-3-methyl-1-<(phenylmethoxy)methyl>-7-oxabicyclo<2.2.1>heptan-2-ol

Refernces