(R)-4-(hydroxymethyl)-2,4-dimethyl-3-(1-methylethoxy)-2-cyclohexenone

Base Information

• Chemical Name: (R)-4-(hydroxymethyl)-2,4-dimethyl-3-(1-methylethoxy)-2-cyclohexenone
• CAS No.: 180692-62-0
• Molecular Formula: C₁₂H₂₀O₃
• Molecular Weight: 212.289
• Mol file: 180692-62-0.mol

Synonyms:(R)-4-(hydroxymethyl)-2,4-dimethyl-3-(1-methylethoxy)-2-cyclohexenone

Chemical Property of (R)-4-(hydroxymethyl)-2,4-dimethyl-3-(1-methylethoxy)-2-cyclohexenone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-4-(hydroxymethyl)-2,4-dimethyl-3-(1-methylethoxy)-2-cyclohexenone

There total 11 articles about (R)-4-(hydroxymethyl)-2,4-dimethyl-3-(1-methylethoxy)-2-cyclohexenone 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: 81.0%

(R)-2,6-dimethyl-3-(1-methylethoxy)-6-[(phenylmethoxy)methyl]-2-cyclohexenone (180692-66-4) → (R)-4-(hydroxymethyl)-2,4-dimethyl-3-(1-methylethoxy)-2-cyclohexenone (180692-62-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 1.3h;

DOI:10.1021/jo960973a

Reference yield:

(2S)-2,6-dimethyl-5-hepten-1-ol (161512-73-8) → (R)-4-(hydroxymethyl)-2,4-dimethyl-3-(1-methylethoxy)-2-cyclohexenone (180692-62-0)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 95 percent / NaH / 1,2-dimethoxy-ethane / 16.5 h / 20 °C

2.1: O₃ / CH₂Cl₂ / -78 °C

2.2: triphenylphosphine / CH₂Cl₂ / -78 - 20 °C

3.1: 2.57 g / tetrahydrofuran / 0.25 h / 0 - 20 °C

4.1: dimethyl sulfoxide; oxalyl chloride / CH₂Cl₂ / 7.5 h / -78 °C

4.2: 1.79 g / triethylamine / CH₂Cl₂ / -78 - 20 °C

5.1: 97 percent / tetrahydrofuran / 12 h / -78 - 20 °C

6.1: 90 percent / potassium bis(trimethylsilyl)amide / diethyl ether / 12 h

7.1: O₃ / CH₂Cl₂ / -78 °C

7.2: 74 percent / triphenylphosphine / CH₂Cl₂ / -78 - 20 °C

8.1: 4 Angstroem molecular sieves / acetonitrile / 0.5 h / 20 °C

8.2: 78 percent / acetic acid; Ca(OCl)2 / acetonitrile / 3 h

9.1: KHMDS / 1,2-dimethoxy-ethane / 9.5 h / 20 °C

10.1: 69 mg / ethyl acetate; diethyl ether / 8 h / 0 - 20 °C

11.1: 81 percent / H₂ / Pd-C / ethanol / 1.3 h

With oxalyl dichloride; 4 A molecular sieve; hydrogen; potassium hexamethylsilazane; sodium hydride; ozone; dimethyl sulfoxide; palladium on activated charcoal; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; ethanol; dichloromethane; ethyl acetate; acetonitrile; 1.1: Alkylation / 2.1: ozonolysis / 2.2: Reduction / 3.1: Grignard reaction / 4.1: Swern oxidation / 4.2: Swern oxidation / 5.1: Wittig reaction / 6.1: Cyclization / 7.1: ozonolysis / 7.2: Decomposition / 8.1: Addition / 8.2: MacDonald oxidation / 9.1: Claisen cyclization / 10.1: Alkylation / 11.1: Hydrogenolysis;

DOI:10.1021/jo960973a

Reference yield:

(S)-5-(phenylmethoxy)-4-methylpentanal (180692-68-6) → (R)-4-(hydroxymethyl)-2,4-dimethyl-3-(1-methylethoxy)-2-cyclohexenone (180692-62-0)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 2.57 g / tetrahydrofuran / 0.25 h / 0 - 20 °C

2.1: dimethyl sulfoxide; oxalyl chloride / CH₂Cl₂ / 7.5 h / -78 °C

2.2: 1.79 g / triethylamine / CH₂Cl₂ / -78 - 20 °C

3.1: 97 percent / tetrahydrofuran / 12 h / -78 - 20 °C

4.1: 90 percent / potassium bis(trimethylsilyl)amide / diethyl ether / 12 h

5.1: O₃ / CH₂Cl₂ / -78 °C

5.2: 74 percent / triphenylphosphine / CH₂Cl₂ / -78 - 20 °C

6.1: 4 Angstroem molecular sieves / acetonitrile / 0.5 h / 20 °C

6.2: 78 percent / acetic acid; Ca(OCl)2 / acetonitrile / 3 h

7.1: KHMDS / 1,2-dimethoxy-ethane / 9.5 h / 20 °C

8.1: 69 mg / ethyl acetate; diethyl ether / 8 h / 0 - 20 °C

9.1: 81 percent / H₂ / Pd-C / ethanol / 1.3 h

With oxalyl dichloride; 4 A molecular sieve; hydrogen; potassium hexamethylsilazane; ozone; dimethyl sulfoxide; palladium on activated charcoal; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; ethanol; dichloromethane; ethyl acetate; acetonitrile; 1.1: Grignard reaction / 2.1: Swern oxidation / 2.2: Swern oxidation / 3.1: Wittig reaction / 4.1: Cyclization / 5.1: ozonolysis / 5.2: Decomposition / 6.1: Addition / 6.2: MacDonald oxidation / 7.1: Claisen cyclization / 8.1: Alkylation / 9.1: Hydrogenolysis;

DOI:10.1021/jo960973a

upstream raw materials:

(R)-2,6-dimethyl-3-(1-methylethoxy)-6-[(phenylmethoxy)methyl]-2-cyclohexenone

(2S)-2,6-dimethyl-5-hepten-1-ol

(S)-5-(phenylmethoxy)-4-methylpentanal

(S)-(-)-2,6-dimethyl-7-(phenylmethoxy)-2-heptene

Downstream raw materials:

(+)-Cassiol