2-(2-nitrophenyl)-1,4-cyclohexanedione monoethylene acetal

Base Information

• Chemical Name: 2-(2-nitrophenyl)-1,4-cyclohexanedione monoethylene acetal
• CAS No.: 954413-33-3
• Molecular Formula: C₁₄H₁₅NO₅
• Molecular Weight: 277.277
• Mol file: 954413-33-3.mol

Synonyms:

Chemical Property of 2-(2-nitrophenyl)-1,4-cyclohexanedione monoethylene acetal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(2-nitrophenyl)-1,4-cyclohexanedione monoethylene acetal

There total 2 articles about 2-(2-nitrophenyl)-1,4-cyclohexanedione monoethylene acetal 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:

cyclohexanedione monoethylene ketal (4746-97-8) → 2-(2-nitrophenyl)-1,4-cyclohexanedione monoethylene acetal (954413-33-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: LDA / tetrahydrofuran; cyclohexane / 1 h / -78 °C

1.2: tetrahydrofuran; cyclohexane / 1 h / 20 °C

2.1: 4.03 g / dimethylsulfoxide; CH₂Cl₂ / -40 - 20 °C

With lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; cyclohexane; dimethyl sulfoxide;

DOI:10.1016/j.tet.2007.07.098

Reference yield:

1,4-cyclohexanedione-1-ethylene acetal 4-trimethylsilyl enol ether (144810-01-5) + (o-nitrophenyl)phenyliodonium fluoride → 2-(2-nitrophenyl)-1,4-cyclohexanedione monoethylene acetal (954413-33-3)

Guidance literature:

In dichloromethane; dimethyl sulfoxide; at -40 - 20 ℃;

DOI:10.1016/j.tet.2007.07.098

Reference yield:

2-(2-nitrophenyl)-1,4-cyclohexanedione monoethylene acetal (954413-33-3) → C20H26N2O

Guidance literature:

Multi-step reaction with 9 steps

1.1: Cs₂CO₃ / acetone / Heating

2.1: 6.17 g / toluene / 12 h / 180 - 190 °C

3.1: ozone / CH₂Cl₂ / 0.25 h / -78 °C

3.2: 59 percent / sodium cyanoborohydride / methanol

4.1: α-(chloroethyl)chloroformate

4.2: 25 percent / methanol / Heating

5.1: SnCl₂*2H₂O / dimethylformamide / 24 h / 20 °C

6.1: 74 percent / sodium cyanoborohydride; glacial acetic acid / H₂O; acetonitrile / 0.5 h

7.1: aqueous HCl / tetrahydrofuran / 23 h / 20 °C

8.1: 40 mg / t-BuOK / Pd(PPh₃)4 / tetrahydrofuran; 2-methyl-propan-2-ol / 0.75 h / Heating

With hydrogenchloride; potassium tert-butylate; sodium cyanoborohydride; caesium carbonate; ozone; acetic acid; tin(ll) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; tert-butyl alcohol; 2.1: Claisen rearrangement;

DOI:10.1016/j.tet.2007.07.098

upstream raw materials:

1,4-cyclohexanedione-1-ethylene acetal 4-trimethylsilyl enol ether

cyclohexanedione monoethylene ketal

Downstream raw materials:

4-allyloxy-3-(2-nitrophenyl)-3-cyclohexanone ethylene acetal

2-allyl-2-(2-nitrophenyl)-1,4-cyclohexanedione monoethylene acetal