(1R,6R)-5,5-(ethylenedioxy)bicyclo<4.2.0>octane-1-carboxylic acid

Base Information

• Chemical Name: (1R,6R)-5,5-(ethylenedioxy)bicyclo<4.2.0>octane-1-carboxylic acid
• CAS No.: 105616-17-9
• Molecular Formula: C₁₁H₁₆O₄
• Molecular Weight: 212.246
• Mol file: 105616-17-9.mol

Synonyms:

Chemical Property of (1R,6R)-5,5-(ethylenedioxy)bicyclo<4.2.0>octane-1-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,6R)-5,5-(ethylenedioxy)bicyclo<4.2.0>octane-1-carboxylic acid

There total 1 articles about (1R,6R)-5,5-(ethylenedioxy)bicyclo<4.2.0>octane-1-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:

C11H15ClO3 (109272-32-4) → 1-Phenylethanol (98-85-1,13323-81-4) + 5-Hydroxy-bicyclo[4.2.0]octane-1-carboxylic acid + C11H16O4 (105616-17-9,105616-18-0)

Guidance literature:

With potassium hydroxide; (S)-1-phenyl-ethylamine; Yield given; 2.) ethylene glicol, 200 deg C, 24 h;;

DOI:10.1016/S0040-4039(00)85102-3

Reference yield:

(1R,6R)-5,5-(ethylenedioxy)bicyclo<4.2.0>octane-1-carboxylic acid (105539-60-4,105616-17-9,105616-18-0) → (1R, 2S)-grandisol (26532-22-9)

Guidance literature:

Multi-step reaction with 11 steps

1: 82 percent / LiAlH₄ / diethyl ether / 1 h / Ambient temperature

2: 96 percent / pyridine / 24 h / 0 °C

3: 81 percent / lithium triethylborohydride / tetrahydrofuran / 14 h / Ambient temperature

4: 87 percent / HCl / diethyl ether / 12 h

5: ethyl acetate / 0.33 h

6: PTSA / benzene / 4 h / Heating

7: H₂O₂ / CH₂Cl₂; pyridine / 1.5 h / Ambient temperature

8: 84 percent / diethyl ether / 0 °C

9: 61 percent / sodium periodate, ruthenium(III) chloride / CCl₄; acetonitrile; H₂O / 5 h

10: 1.) BuLi / 1.) THF, hexane, 1 h, 2.) THF, RT, 2.5 h

11: 70 percent / LiAlH₄ / diethyl ether / 1 h / Ambient temperature

With hydrogenchloride; ruthenium trichloride; sodium periodate; lithium aluminium tetrahydride; n-butyllithium; dihydrogen peroxide; lithium triethylborohydride; toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; tetrachloromethane; diethyl ether; dichloromethane; water; ethyl acetate; acetonitrile; benzene;

DOI:10.1021/jo00376a033

Reference yield:

(1S,6S)-5,5-(ethylenedioxy)bicyclo<4.2.0>octane-1-carboxylic acid (105539-60-4,105616-17-9,105616-18-0) → (1S,6R)-6-Methyl-3-phenylselanyl-bicyclo[4.2.0]octan-2-one (105539-68-2,105616-29-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 86 percent / LiAlH₄ / diethyl ether / 1 h / Ambient temperature

2: 95 percent / pyridine / 24 h / 0 °C

3: 81 percent / lithium triethylborohydride / tetrahydrofuran / 14 h / Ambient temperature

4: 90 percent / HCl / diethyl ether / 12 h

5: ethyl acetate / 0.33 h

With hydrogenchloride; lithium aluminium tetrahydride; lithium triethylborohydride; In tetrahydrofuran; pyridine; diethyl ether; ethyl acetate;

DOI:10.1021/jo00376a033

upstream raw materials:

C₁₁H₁₅ClO₃

Downstream raw materials:

2-[(1S,2R)-1-methyl-2-(prop-1-en-2-yl)cyclobutyl]acetic acid

(1S,6R)-6-Methyl-3-phenylselanyl-bicyclo[4.2.0]octan-2-one

C₁₇H₂₂O₂Se

(1S,6S)-5,5-(ethylenedioxy)-1-(hydroxymethyl)bicyclo<4.2.0>octane p-toluenesulfonate