(1R,2R,3S,4S)-3-(5-Hydroxy-5-methyl-hexyl)-2,4-dimethyl-cyclohexanecarbaldehyde

Base Information

• Chemical Name: (1R,2R,3S,4S)-3-(5-Hydroxy-5-methyl-hexyl)-2,4-dimethyl-cyclohexanecarbaldehyde
• CAS No.: 331961-42-3
• Molecular Formula: C₁₆H₃₀O₂
• Molecular Weight: 254.413

Synonyms:(1R,2R,3S,4S)-3-(5-Hydroxy-5-methyl-hexyl)-2,4-dimethyl-cyclohexanecarbaldehyde

Chemical Property of (1R,2R,3S,4S)-3-(5-Hydroxy-5-methyl-hexyl)-2,4-dimethyl-cyclohexanecarbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R,3S,4S)-3-(5-Hydroxy-5-methyl-hexyl)-2,4-dimethyl-cyclohexanecarbaldehyde

There total 13 articles about (1R,2R,3S,4S)-3-(5-Hydroxy-5-methyl-hexyl)-2,4-dimethyl-cyclohexanecarbaldehyde 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: 66.0%

6-((1S,2R,3R,6S)-3-Hydroxymethyl-2,6-dimethyl-cyclohexyl)-2-methyl-hexan-2-ol (331961-40-1) → (1R,2R,3S,4S)-3-(5-Hydroxy-5-methyl-hexyl)-2,4-dimethyl-cyclohexanecarbaldehyde (331961-42-3)

Guidance literature:

With aluminum oxide; pyridinium chlorochromate; In dichloromethane; for 5h;

DOI:10.1002/1521-3765(20010119)7:2<520::AID-CHEM520>3.0.CO;2-5

Reference yield:

(6S,5R)-2,6-dimethyl-5-(1-methylethenyl)-2-cyclohexen-1-one (91781-46-3) → (1R,2R,3S,4S)-3-(5-Hydroxy-5-methyl-hexyl)-2,4-dimethyl-cyclohexanecarbaldehyde (331961-42-3)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 18 percent / aq. NaHCO₃; sodium dithionite / Adogen 464 / toluene / 2 h / Heating

2.1: EtMgBr / toluene; tetrahydrofuran / 0 - 60 °C

2.2: toluene; tetrahydrofuran / 2 h / Heating

2.3: 70 percent / aq. H₂SO₄ / tetrahydrofuran / 10 h

3.1: Mg; methanol

4.1: LiAlH₄ / tetrahydrofuran

5.1: O₃ / CH₂Cl₂; methanol / 0 °C

5.2: dimethylsulfide / CH₂Cl₂; methanol

6.1: trimethylorthoformate; p-TsOH

7.1: Et₃N; DMAP / CH₂Cl₂

8.1: NaH / dimethylsulfoxide

8.2: dimethylsulfoxide; tetrahydrofuran

9.1: H₂ / 5percent Rh/Al₂O₃ / ethyl acetate

10.1: aq. pyridinium p-toluenesulfonate / Heating

11.1: 46 percent / NaBr / 0.75 h / 0 °C / Electrochemical reaction

12.1: 52 percent / LiAlH₄ / tetrahydrofuran / 3 h / 25 °C

13.1: 66 percent / pyridinium chlorochromate/Al₂O₃ / CH₂Cl₂ / 5 h

With methanol; dmap; aluminum oxide; lithium aluminium tetrahydride; sodium dithionite; ethylmagnesium bromide; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; ozone; magnesium; triethylamine; pyridinium chlorochromate; sodium bromide; trimethyl orthoformate; adogen 464; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; toluene;

DOI:10.1002/1521-3765(20010119)7:2<520::AID-CHEM520>3.0.CO;2-5

Reference yield:

Ethyl [(E,2S,3R,6S)-2,6-dimethyl-3-isopropenylcyclohexylidene]acetate (331961-18-3) → (1R,2R,3S,4S)-3-(5-Hydroxy-5-methyl-hexyl)-2,4-dimethyl-cyclohexanecarbaldehyde (331961-42-3)

Guidance literature:

Multi-step reaction with 11 steps

1.1: Mg; methanol

2.1: LiAlH₄ / tetrahydrofuran

3.1: O₃ / CH₂Cl₂; methanol / 0 °C

3.2: dimethylsulfide / CH₂Cl₂; methanol

4.1: trimethylorthoformate; p-TsOH

5.1: Et₃N; DMAP / CH₂Cl₂

6.1: NaH / dimethylsulfoxide

6.2: dimethylsulfoxide; tetrahydrofuran

7.1: H₂ / 5percent Rh/Al₂O₃ / ethyl acetate

8.1: aq. pyridinium p-toluenesulfonate / Heating

9.1: 46 percent / NaBr / 0.75 h / 0 °C / Electrochemical reaction

10.1: 52 percent / LiAlH₄ / tetrahydrofuran / 3 h / 25 °C

11.1: 66 percent / pyridinium chlorochromate/Al₂O₃ / CH₂Cl₂ / 5 h

With methanol; dmap; aluminum oxide; lithium aluminium tetrahydride; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; toluene-4-sulfonic acid; ozone; magnesium; triethylamine; pyridinium chlorochromate; sodium bromide; trimethyl orthoformate; 5percent Rh/Al₂O₃; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; ethyl acetate;

DOI:10.1002/1521-3765(20010119)7:2<520::AID-CHEM520>3.0.CO;2-5

upstream raw materials:

6-((1S,2R,3R,6S)-3-Hydroxymethyl-2,6-dimethyl-cyclohexyl)-2-methyl-hexan-2-ol

(6S,5R)-2,6-dimethyl-5-(1-methylethenyl)-2-cyclohexen-1-one

(2S,3R,6S)-2,6-dimethyl-3-(prop-1-en-2-yl)cyclohexan-1-one

Ethyl [(E,2S,3R,6S)-2,6-dimethyl-3-isopropenylcyclohexylidene]acetate

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