Cyclohexanecarboxaldehyde, 3-(1,1-dimethylethyl)-1,2-dimethyl-, (1R,2R,3S)-

Base Information

• Chemical Name: Cyclohexanecarboxaldehyde, 3-(1,1-dimethylethyl)-1,2-dimethyl-, (1R,2R,3S)-
• CAS No.: 877659-71-7
• Molecular Formula: C13H24O
• Molecular Weight: 196.333
• Mol file: 877659-71-7.mol

Synonyms:

Chemical Property of Cyclohexanecarboxaldehyde, 3-(1,1-dimethylethyl)-1,2-dimethyl-, (1R,2R,3S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Cyclohexanecarboxaldehyde, 3-(1,1-dimethylethyl)-1,2-dimethyl-, (1R,2R,3S)-

There total 9 articles about Cyclohexanecarboxaldehyde, 3-(1,1-dimethylethyl)-1,2-dimethyl-, (1R,2R,3S)- 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:

1,6-dimethyl-cyclohex-3-enecarbaldehyde (877659-54-6) → (1R,2R,3S)-3-tert-Butyl-1,2-dimethyl-cyclohexanecarbaldehyde (877659-71-7)

Guidance literature:

Multi-step reaction with 9 steps

1.1: Jones' reagent / acetone / 1 h / 0 °C

2.1: aq. NaHCO₃; KI; I₂ / tetrahydrofuran / 6 h / 0 °C

3.1: DBU / tetrahydrofuran / 12 h / Heating

4.1: methanol / 3 h / 20 °C

5.1: pyridinium chlorochromate / CH₂Cl₂ / 1 h / 20 °C

6.1: CuCN / tetrahydrofuran; pentane / 1 h / -78 °C

6.2: Me₃SiCl / pentane; tetrahydrofuran / 2 h / -78 °C

7.1: tosyl hydrazide; p-TsOH; NaBH₃CN / dimethylformamide; tetrahydrothiophene 1,1-dioxide / 2 h / 100 °C

8.1: diisobutylaluminum hydride / CH₂Cl₂ / 1 h / -78 °C

9.1: pyridinium chlorochromate / CH₂Cl₂ / 1 h / 20 °C

With jones' reagent; iodine; diisobutylaluminium hydride; sodium cyanoborohydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; toluene-4-sulfonic acid hydrazide; pyridinium chlorochromate; potassium iodide; In tetrahydrofuran; sulfolane; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; pentane;

DOI:10.1021/ja057483x

Reference yield:

5-hydroxy-1,2-dimethyl-cyclohex-3-enecarboxylic acid lactone (421555-41-1) → (1R,2R,3S)-3-tert-Butyl-1,2-dimethyl-cyclohexanecarbaldehyde (877659-71-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: methanol / 3 h / 20 °C

2.1: pyridinium chlorochromate / CH₂Cl₂ / 1 h / 20 °C

3.1: CuCN / tetrahydrofuran; pentane / 1 h / -78 °C

3.2: Me₃SiCl / pentane; tetrahydrofuran / 2 h / -78 °C

4.1: tosyl hydrazide; p-TsOH; NaBH₃CN / dimethylformamide; tetrahydrothiophene 1,1-dioxide / 2 h / 100 °C

5.1: diisobutylaluminum hydride / CH₂Cl₂ / 1 h / -78 °C

6.1: pyridinium chlorochromate / CH₂Cl₂ / 1 h / 20 °C

With diisobutylaluminium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; toluene-4-sulfonic acid hydrazide; pyridinium chlorochromate; In tetrahydrofuran; sulfolane; methanol; dichloromethane; N,N-dimethyl-formamide; pentane;

DOI:10.1021/ja057483x

Reference yield:

1,2-dimethyl-5-oxo-cyclohex-3-enecarboxylic acid methyl ester (877659-55-7) → (1R,2R,3S)-3-tert-Butyl-1,2-dimethyl-cyclohexanecarbaldehyde (877659-71-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: CuCN / tetrahydrofuran; pentane / 1 h / -78 °C

1.2: Me₃SiCl / pentane; tetrahydrofuran / 2 h / -78 °C

2.1: tosyl hydrazide; p-TsOH; NaBH₃CN / dimethylformamide; tetrahydrothiophene 1,1-dioxide / 2 h / 100 °C

3.1: diisobutylaluminum hydride / CH₂Cl₂ / 1 h / -78 °C

4.1: pyridinium chlorochromate / CH₂Cl₂ / 1 h / 20 °C

With diisobutylaluminium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; toluene-4-sulfonic acid hydrazide; pyridinium chlorochromate; In tetrahydrofuran; sulfolane; dichloromethane; N,N-dimethyl-formamide; pentane;

DOI:10.1021/ja057483x

upstream raw materials:

1,6-dimethyl-cyclohex-3-enecarbaldehyde

5-hydroxy-1,2-dimethyl-cyclohex-3-enecarboxylic acid lactone

1,2-dimethyl-5-oxo-cyclohex-3-enecarboxylic acid methyl ester

(1R,2R,5S)-5-Hydroxy-1,2-dimethyl-cyclohex-3-enecarboxylic acid methyl ester