(R)-(+)-4-pentyl-3-cyclohexene-1-carboxylic acid

Base Information

• Chemical Name: (R)-(+)-4-pentyl-3-cyclohexene-1-carboxylic acid
• CAS No.: 146659-04-3
• Molecular Formula: C₁₂H₂₀O₂
• Molecular Weight: 196.29
• Mol file: 146659-04-3.mol

Synonyms:(R)-(+)-4-pentyl-3-cyclohexene-1-carboxylic acid

Chemical Property of (R)-(+)-4-pentyl-3-cyclohexene-1-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-(+)-4-pentyl-3-cyclohexene-1-carboxylic acid

There total 14 articles about (R)-(+)-4-pentyl-3-cyclohexene-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:

beta-pinene (18172-67-3,19902-08-0,25719-60-2) → (R)-(+)-4-pentyl-3-cyclohexene-1-carboxylic acid (146659-04-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 35 percent / potassium bicarbonate, benzonitrile, 30percent hydrogen peroxide / methanol / 24 h / Ambient temperature

2: ammonium nitrate / nitromethane / 4 h / 80 °C

3: 90 percent / pyridine / diethyl ether / 4 h / Ambient temperature

4: 1) cuprous iodide / 1) diethyl ether, hexane, 0 deg C, 10 min 2) diethyl ether, -40 deg C, 2 h

5: 60 percent / methyltrioctylammonium chloride, magnesium monoperoxyphthalic acid / H₂O; CHCl₃ / 5 h / 50 °C

6: 1) ozone, 2) zinc dust, sodium acetate, sodium iodide / 1) CH₂Cl₂, -78 deg C, 2) glacial acetic acid, 0 deg C up to r.t., overnight

7: 10percent aqueous sodium hydroxide, iodine-potassium iodide-water / H₂O; dioxane / a) r.t., 1 h, b) 60 deg C, 1 h

With pyridine; sodium hydroxide; copper(l) iodide; ammonium nitrate; dihydrogen peroxide; iodine; sodium acetate; Aliquat 336; potassium hydrogencarbonate; magnesium monoperoxyphthalate hexahydrate; ozone; benzonitrile; potassium iodide; sodium iodide; zinc; In 1,4-dioxane; methanol; diethyl ether; nitromethane; chloroform; water;

DOI:10.1016/S0040-4020(01)86265-7

Reference yield:

(1R,5R)-(+)-β-pinene (127-91-3,25719-60-2) → (R)-(+)-4-pentyl-3-cyclohexene-1-carboxylic acid (146659-04-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 35 percent / potassium bicarbonate, benzonitrile, 30percent hydrogen peroxide / methanol / 24 h / Ambient temperature

2: ammonium nitrate / nitromethane / 4 h / 80 °C

3: 90 percent / pyridine / diethyl ether / 4 h / Ambient temperature

4: 1) cuprous iodide / 1) diethyl ether, hexane, 0 deg C, 10 min 2) diethyl ether, -40 deg C, 2 h

5: 60 percent / methyltrioctylammonium chloride, magnesium monoperoxyphthalic acid / H₂O; CHCl₃ / 5 h / 50 °C

6: 1) ozone, 2) zinc dust, sodium acetate, sodium iodide / 1) CH₂Cl₂, -78 deg C, 2) glacial acetic acid, 0 deg C up to r.t., overnight

7: 10percent aqueous sodium hydroxide, iodine-potassium iodide-water / H₂O; dioxane / a) r.t., 1 h, b) 60 deg C, 1 h

With pyridine; sodium hydroxide; copper(l) iodide; ammonium nitrate; dihydrogen peroxide; iodine; sodium acetate; Aliquat 336; potassium hydrogencarbonate; magnesium monoperoxyphthalate hexahydrate; ozone; benzonitrile; potassium iodide; sodium iodide; zinc; In 1,4-dioxane; methanol; diethyl ether; nitromethane; chloroform; water;

DOI:10.1016/S0040-4020(01)86265-7

Reference yield:

trans-2,10-epoxypinane (6931-54-0) → (R)-(+)-4-pentyl-3-cyclohexene-1-carboxylic acid (146659-04-3)

Guidance literature:

Multi-step reaction with 6 steps

1: ammonium nitrate / nitromethane / 4 h / 80 °C

2: 90 percent / pyridine / diethyl ether / 4 h / Ambient temperature

3: 1) cuprous iodide / 1) diethyl ether, hexane, 0 deg C, 10 min 2) diethyl ether, -40 deg C, 2 h

4: 60 percent / methyltrioctylammonium chloride, magnesium monoperoxyphthalic acid / H₂O; CHCl₃ / 5 h / 50 °C

5: 1) ozone, 2) zinc dust, sodium acetate, sodium iodide / 1) CH₂Cl₂, -78 deg C, 2) glacial acetic acid, 0 deg C up to r.t., overnight

6: 10percent aqueous sodium hydroxide, iodine-potassium iodide-water / H₂O; dioxane / a) r.t., 1 h, b) 60 deg C, 1 h

With pyridine; sodium hydroxide; copper(l) iodide; ammonium nitrate; iodine; sodium acetate; Aliquat 336; magnesium monoperoxyphthalate hexahydrate; ozone; potassium iodide; sodium iodide; zinc; In 1,4-dioxane; diethyl ether; nitromethane; chloroform; water;

DOI:10.1016/S0040-4020(01)86265-7

upstream raw materials:

(R)-(+)-1-pentyl-4-acetyl-1-cyclohexene

(S)-(-)-1-pentyl-4-acetyl-1-cyclohexene

beta-pinene

(R)-Perillyl alcohol

Refernces