(R)-2,2,4-trimethyl-3-cyclohexen-1-acetonitrile

Base Information

• Chemical Name: (R)-2,2,4-trimethyl-3-cyclohexen-1-acetonitrile
• CAS No.: 108361-17-7
• Molecular Formula: C₁₁H₁₇N
• Molecular Weight: 163.263
• Mol file: 108361-17-7.mol

Synonyms:(R)-2,2,4-trimethyl-3-cyclohexen-1-acetonitrile

Chemical Property of (R)-2,2,4-trimethyl-3-cyclohexen-1-acetonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2,2,4-trimethyl-3-cyclohexen-1-acetonitrile

There total 1 articles about (R)-2,2,4-trimethyl-3-cyclohexen-1-acetonitrile 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: 82.0%

sodium cyanide (143-33-9,25596-52-5) + Toluene-4-sulfonic acid (R)-2,2,4-trimethyl-cyclohex-3-enylmethyl ester → (R)-2,2,4-trimethyl-3-cyclohexen-1-acetonitrile (108361-17-7)

Guidance literature:

In N,N-dimethyl-formamide; at 70 ℃; for 23h;

DOI:10.1002/hlca.19860690315

Reference yield: 93.0%

(R)-2,2,4-trimethyl-3-cyclohexen-1-acetonitrile (108361-17-7) → (R)-2,2,4-trimethyl-3-cyclohexen-1-acetaldehyde (108361-18-8)

Guidance literature:

With diisobutylaluminium hydride; In hexane; 1.) -60 deg C, 2.) RT, 1 h;

DOI:10.1002/hlca.19860690315

Reference yield:

(R)-2,2,4-trimethyl-3-cyclohexen-1-acetonitrile (108361-17-7) → (R)-4-<5'-(3-methyl-2-butenyl)-2',6',6'-trimethyl-1'-cyclohexenyl>-3-buten-2-one (108394-26-9)

Guidance literature:

Multi-step reaction with 12 steps

1: 93 percent / DIBAH / hexane / 1.) -60 deg C, 2.) RT, 1 h

2: 95 percent / PPTS / benzene / 23 h / Heating

3: 1.) Me₂S*BH₃, 3.) 30percent H₂O₂, 3N NaOH / 1.) ether, 0 deg C, 15 min, 2.) RT, 4 h, 3.) reflux, 1 h

4: 82 percent / CrO₃, pyridine / CH₂Cl₂ / 0.25 h

5: 99 percent / H₂O / PPTS / acetone / 48 h / Heating

6: 49 percent / BuLi / tetrahydrofuran; hexane / 0 deg C - 5 deg C, 20 min

7: 95 percent / EtMgBr / diethyl ether; benzene / 1 h / Heating

8: TFA / 23 h / Ambient temperature

9: BuLi / tetrahydrofuran; hexane / -10 °C

10: PPTS / dimethylformamide / 2 h / 80 °C

11: 95 percent / LiAlH₄ / tetrahydrofuran / 18 h / Heating

12: 95 percent / MnO₂ / diethyl ether / 15 h / Ambient temperature

With pyridine; chromium(VI) oxide; manganese(IV) oxide; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; dimethylsulfide borane complex; ethylmagnesium bromide; water; dihydrogen peroxide; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; trifluoroacetic acid; pyridinium p-toluenesulfonate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1002/hlca.19860690315

upstream raw materials:

sodium cyanide

Downstream raw materials:

(R)-2,2,4-trimethyl-3-cyclohexen-1-acetaldehyde

(all-E,2R,2'R)-2,2'-bis(4-hydroxy-3-methyl-2-butenyl)-β,β-carotin

(3R)-3-oxo-2,2,4-trimethylcyclohexan-1-acetaldehyde

(3R)-3-(3'-methyl-2'-butenyl)-2,2,6-trimethylcyclohexanone