4-Cyclodecene-1-carboxylic acid, 5-methyl-8-(1-methylethyl)-1-(phenylthio)-, methyl ester

Base Information

• Chemical Name: 4-Cyclodecene-1-carboxylic acid, 5-methyl-8-(1-methylethyl)-1-(phenylthio)-, methyl ester
• CAS No.: 91201-50-2
• Molecular Formula: C₂₂H₃₂O₂S
• Molecular Weight: 360.561
• Mol file: 91201-50-2.mol

Synonyms:

Chemical Property of 4-Cyclodecene-1-carboxylic acid, 5-methyl-8-(1-methylethyl)-1-(phenylthio)-, methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Cyclodecene-1-carboxylic acid, 5-methyl-8-(1-methylethyl)-1-(phenylthio)-, methyl ester

There total 13 articles about 4-Cyclodecene-1-carboxylic acid, 5-methyl-8-(1-methylethyl)-1-(phenylthio)-, methyl 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:

(3R)-6,6-(Ethylenedioxy)-3-(1-methylethyl)-1-heptanol (91201-42-2) → Methyl <1(R,S),4(E,Z),8R>-5-Methyl-8-(1-methylethyl)-1-(phenylthio)-4-cyclodecenecarboxylate (91201-50-2)

Guidance literature:

Multi-step reaction with 10 steps

1: 52 g / pyridine / Ambient temperature

2: 35percent HClO₄ / tetrahydrofuran / 0.08 h / 0 °C

3: 1) Mg / 1) THF, 2) THF, -5 to 0 deg C

4: 47percent aqueous HBr / 0.17 h / < 0 deg C

5: 71 percent / 50percent NaOH / n-Bu₄NBr / benzene / 0.67 h / Heating

6: NaOMe / methanol / 0.5 h / Ambient temperature

7: 81 percent / pyridine / 3 h / 0 °C

8: 80 percent / NaN(SiMe₃)2 / 1,2-dimethoxy-ethane / Heating

9: aqueous KOH / 2-methoxy-ethanol; ethane-1,2-diol / 48 h / 170 - 175 °C

10: diethyl ether

With pyridine; potassium hydroxide; sodium hydroxide; perchloric acid; hydrogen bromide; sodium methylate; sodium hexamethyldisilazane; magnesium; tetrabutylammomium bromide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; 2-methoxy-ethanol; ethylene glycol; benzene;

DOI:10.1021/jo00192a007

Reference yield:

(R)-(+)-3-isopropyl-6-oxoheptanoic acid (80845-81-4) → Methyl <1(R,S),4(E,Z),8R>-5-Methyl-8-(1-methylethyl)-1-(phenylthio)-4-cyclodecenecarboxylate (91201-50-2)

Guidance literature:

Multi-step reaction with 13 steps

1: diethyl ether / 0.08 h

2: 98 percent / p-TsOH / benzene / Heating

3: 43.6 g / LiAlH₄ / diethyl ether / 1) -5 to 0 deg C 2) 0-10 deg C

4: 52 g / pyridine / Ambient temperature

5: 35percent HClO₄ / tetrahydrofuran / 0.08 h / 0 °C

6: 1) Mg / 1) THF, 2) THF, -5 to 0 deg C

7: 47percent aqueous HBr / 0.17 h / < 0 deg C

8: 71 percent / 50percent NaOH / n-Bu₄NBr / benzene / 0.67 h / Heating

9: NaOMe / methanol / 0.5 h / Ambient temperature

10: 81 percent / pyridine / 3 h / 0 °C

11: 80 percent / NaN(SiMe₃)2 / 1,2-dimethoxy-ethane / Heating

12: aqueous KOH / 2-methoxy-ethanol; ethane-1,2-diol / 48 h / 170 - 175 °C

13: diethyl ether

With pyridine; potassium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; perchloric acid; hydrogen bromide; sodium methylate; sodium hexamethyldisilazane; magnesium; tetrabutylammomium bromide; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; 2-methoxy-ethanol; ethylene glycol; benzene;

DOI:10.1021/jo00192a007

Reference yield:

Methyl (3R)-6,6-(ethylenedioxy)-3-(1-methylethyl)heptanoate (91201-41-1) → Methyl <1(R,S),4(E,Z),8R>-5-Methyl-8-(1-methylethyl)-1-(phenylthio)-4-cyclodecenecarboxylate (91201-50-2)

Guidance literature:

Multi-step reaction with 11 steps

1: 43.6 g / LiAlH₄ / diethyl ether / 1) -5 to 0 deg C 2) 0-10 deg C

2: 52 g / pyridine / Ambient temperature

3: 35percent HClO₄ / tetrahydrofuran / 0.08 h / 0 °C

4: 1) Mg / 1) THF, 2) THF, -5 to 0 deg C

5: 47percent aqueous HBr / 0.17 h / < 0 deg C

6: 71 percent / 50percent NaOH / n-Bu₄NBr / benzene / 0.67 h / Heating

7: NaOMe / methanol / 0.5 h / Ambient temperature

8: 81 percent / pyridine / 3 h / 0 °C

9: 80 percent / NaN(SiMe₃)2 / 1,2-dimethoxy-ethane / Heating

10: aqueous KOH / 2-methoxy-ethanol; ethane-1,2-diol / 48 h / 170 - 175 °C

11: diethyl ether

With pyridine; potassium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; perchloric acid; hydrogen bromide; sodium methylate; sodium hexamethyldisilazane; magnesium; tetrabutylammomium bromide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; 2-methoxy-ethanol; ethylene glycol; benzene;

DOI:10.1021/jo00192a007

upstream raw materials:

(3R)-6,6-(Ethylenedioxy)-3-(1-methylethyl)-1-heptanol

Methyl (3R)-6,6-(ethylenedioxy)-3-(1-methylethyl)heptanoate

(R)-(+)-3-isopropyl-6-oxoheptanoic acid

Methyl (R)-3-(1-methylethyl)-6-oxoheptanoate

Refernces