(6S)-3-(α-acetoxyethylidene)-6-methylcyclohexyl acetate

Base Information

• Chemical Name: (6S)-3-(α-acetoxyethylidene)-6-methylcyclohexyl acetate
• CAS No.: 112655-37-5
• Molecular Formula: C₁₃H₂₀O₄
• Molecular Weight: 240.299
• Mol file: 112655-37-5.mol

Synonyms:

Chemical Property of (6S)-3-(α-acetoxyethylidene)-6-methylcyclohexyl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6S)-3-(α-acetoxyethylidene)-6-methylcyclohexyl acetate

There total 4 articles about (6S)-3-(α-acetoxyethylidene)-6-methylcyclohexyl acetate 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: 60.0%

acetic anhydride (108-24-7) + (3S,6S)-3-acetyl-6-methylcyclohexyl acetate (112655-35-3,112655-36-4,112655-41-1,112655-42-2) → (6S)-3-(α-acetoxyethylidene)-6-methylcyclohexyl acetate (112655-37-5,112655-38-6,112655-39-7,112680-33-8)

Guidance literature:

With toluene-4-sulfonic acid; at 90 ℃; for 6h;

DOI:10.1021/jo00240a033

Reference yield:

(3S,6S)-3-isopropenyl-6-methylcyclohexanol (619-01-2,18675-33-7,18675-34-8,18675-35-9,20549-47-7,20549-48-8,22567-21-1,22567-22-2,36237-64-6,38049-26-2,51773-45-6,53796-77-3,53796-80-8,73804-29-2,17699-09-1) → (6S)-3-(α-acetoxyethylidene)-6-methylcyclohexyl acetate (112655-37-5,112655-38-6,112655-39-7,112680-33-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / pyridine / 3 h / 85 °C

2: 1.) ozone, 2.) zinc, acetic acid / 1.) MeOH, CH₂Cl₂, a) -78 deg C, 15 min, b) 25 deg C, 30 min, 2.) 25 deg C, 30 min

3: 60 percent / p-TsOH / 6 h / 90 °C

With pyridine; toluene-4-sulfonic acid; ozone; acetic acid; zinc;

DOI:10.1021/jo00240a033

Reference yield:

(S)-p-mentha-6,8-dien-2-one (2244-16-8,6485-40-1) → (6S)-3-(α-acetoxyethylidene)-6-methylcyclohexyl acetate (112655-37-5,112655-38-6,112655-39-7,112680-33-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 73.1 percent / Li, liquid NH₃, t-BuOH / tetrahydrofuran / 0.25 h / -35 °C

2: 92 percent / Dibal-H / toluene / 2 h / -78 °C

3: 89 percent / pyridine / 3 h / 85 °C

4: 1.) ozone, 2.) zinc, acetic acid / 1.) MeOH, CH₂Cl₂, a) -78 deg C, 15 min, b) 25 deg C, 30 min, 2.) 25 deg C, 30 min

5: 60 percent / p-TsOH / 6 h / 90 °C

With pyridine; ammonia; lithium; diisobutylaluminium hydride; toluene-4-sulfonic acid; ozone; acetic acid; zinc; tert-butyl alcohol; In tetrahydrofuran; toluene;

DOI:10.1021/jo00240a033

upstream raw materials:

acetic anhydride

(3S,6S)-3-acetyl-6-methylcyclohexyl acetate

(S)-p-mentha-6,8-dien-2-one

(-)-dihydrocarvone

Downstream raw materials:

(3R,4S)-cis-3-acetoxy-4-methylcyclohexanone

(3S,4S)-trans-3-acetoxy-4-methylcyclohexanone