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

Base Information

• Chemical Name: 6-((1S,2R,3R,6R)-3-Hydroxymethyl-2,6-dimethyl-cyclohexyl)-2-methyl-hexan-2-ol
• CAS No.: 331961-30-9
• Molecular Formula: C₁₆H₃₂O₂
• Molecular Weight: 256.429

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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

There total 14 articles about 6-((1S,2R,3R,6R)-3-Hydroxymethyl-2,6-dimethyl-cyclohexyl)-2-methyl-hexan-2-ol 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: 99.0%

(1R,2R,3S,4R)-3-(5-Hydroxy-5-methyl-hexyl)-2,4-dimethyl-cyclohexanecarboxylic acid methyl ester (331961-29-6) → 6-((1S,2R,3R,6R)-3-Hydroxymethyl-2,6-dimethyl-cyclohexyl)-2-methyl-hexan-2-ol (331961-30-9)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 25 ℃; for 3h;

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) → 6-((1S,2R,3R,6R)-3-Hydroxymethyl-2,6-dimethyl-cyclohexyl)-2-methyl-hexan-2-ol (331961-30-9)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 80 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: 44 percent / aq. H₂SO₄ / tetrahydrofuran / 10 h

3.1: Mg; methanol

4.1: 97 percent / LiAlH₄ / tetrahydrofuran / 3 h / 25 °C

5.1: O₃ / CH₂Cl₂; methanol / -40 °C

5.2: 89 percent / dimethylsulfide / CH₂Cl₂; methanol / 25 °C

6.1: 83 percent / trimethylorthoformate; p-TsOH / 2 h / 25 °C

7.1: 97 percent / Et₃N; DMAP / CH₂Cl₂ / 20 h / 25 °C

8.1: NaH / dimethylsulfoxide / 0.07 h

8.2: 77 percent / dimethylsulfoxide; tetrahydrofuran / 2 h

9.1: 75 percent / H₂ / 5percent Rh/Al₂O₃ / ethyl acetate

10.1: 92 percent / aq. pyridinium p-toluenesulfonate / 20 h / Heating

11.1: 28 percent / NaBr / 0.75 h / 0 °C / Electrochemical reaction

12.1: 99 percent / LiAlH₄ / tetrahydrofuran / 3 h / 25 °C

With methanol; dmap; lithium aluminium tetrahydride; sodium dithionite; ethylmagnesium bromide; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; ozone; magnesium; triethylamine; 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:

(2S,3R,6R)-2,6-dimethyl-3-(prop-1-en-2-yl)cyclohexan-1-one (331961-14-9) → 6-((1S,2R,3R,6R)-3-Hydroxymethyl-2,6-dimethyl-cyclohexyl)-2-methyl-hexan-2-ol (331961-30-9)

Guidance literature:

Multi-step reaction with 11 steps

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

1.2: toluene; tetrahydrofuran / 2 h / Heating

1.3: 44 percent / aq. H₂SO₄ / tetrahydrofuran / 10 h

2.1: Mg; methanol

3.1: 97 percent / LiAlH₄ / tetrahydrofuran / 3 h / 25 °C

4.1: O₃ / CH₂Cl₂; methanol / -40 °C

4.2: 89 percent / dimethylsulfide / CH₂Cl₂; methanol / 25 °C

5.1: 83 percent / trimethylorthoformate; p-TsOH / 2 h / 25 °C

6.1: 97 percent / Et₃N; DMAP / CH₂Cl₂ / 20 h / 25 °C

7.1: NaH / dimethylsulfoxide / 0.07 h

7.2: 77 percent / dimethylsulfoxide; tetrahydrofuran / 2 h

8.1: 75 percent / H₂ / 5percent Rh/Al₂O₃ / ethyl acetate

9.1: 92 percent / aq. pyridinium p-toluenesulfonate / 20 h / Heating

10.1: 28 percent / NaBr / 0.75 h / 0 °C / Electrochemical reaction

11.1: 99 percent / LiAlH₄ / tetrahydrofuran / 3 h / 25 °C

With methanol; dmap; lithium aluminium tetrahydride; ethylmagnesium bromide; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; toluene-4-sulfonic acid; ozone; magnesium; triethylamine; sodium bromide; trimethyl orthoformate; 5percent Rh/Al₂O₃; 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

upstream raw materials:

(1R,2R,3S,4R)-3-(5-Hydroxy-5-methyl-hexyl)-2,4-dimethyl-cyclohexanecarboxylic acid methyl ester

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

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

1-[(1R,2R,3S,6R)-3-(2-Hydroxyethyl)-2,4-dimethylcyclohexyl]ethanone

Downstream raw materials:

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

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