1-[(1R,2R,3S,4S)-3-(5-Hydroxy-5-methyl-hexyl)-2,4-dimethyl-cyclohexyl]-ethanone

Base Information

• Chemical Name: 1-[(1R,2R,3S,4S)-3-(5-Hydroxy-5-methyl-hexyl)-2,4-dimethyl-cyclohexyl]-ethanone
• CAS No.: 331961-36-5
• Molecular Formula: C₁₇H₃₂O₂
• Molecular Weight: 268.44

Synonyms:1-[(1R,2R,3S,4S)-3-(5-Hydroxy-5-methyl-hexyl)-2,4-dimethyl-cyclohexyl]-ethanone

Chemical Property of 1-[(1R,2R,3S,4S)-3-(5-Hydroxy-5-methyl-hexyl)-2,4-dimethyl-cyclohexyl]-ethanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of 1-[(1R,2R,3S,4S)-3-(5-Hydroxy-5-methyl-hexyl)-2,4-dimethyl-cyclohexyl]-ethanone

There total 9 articles about 1-[(1R,2R,3S,4S)-3-(5-Hydroxy-5-methyl-hexyl)-2,4-dimethyl-cyclohexyl]-ethanone 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:

(6S,5R)-2,6-dimethyl-5-(1-methylethenyl)-2-cyclohexen-1-one (91781-46-3) → 1-[(1R,2R,3S,4S)-3-(5-Hydroxy-5-methyl-hexyl)-2,4-dimethyl-cyclohexyl]-ethanone (331961-36-5)

Guidance literature:

Multi-step reaction with 10 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

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; 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) → 1-[(1R,2R,3S,4S)-3-(5-Hydroxy-5-methyl-hexyl)-2,4-dimethyl-cyclohexyl]-ethanone (331961-36-5)

Guidance literature:

Multi-step reaction with 8 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

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

Reference yield:

(2S,3R,6S)-2,6-dimethyl-3-(prop-1-en-2-yl)cyclohexan-1-one (331961-46-7) → 1-[(1R,2R,3S,4S)-3-(5-Hydroxy-5-methyl-hexyl)-2,4-dimethyl-cyclohexyl]-ethanone (331961-36-5)

Guidance literature:

Multi-step reaction with 9 steps

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

1.2: toluene; tetrahydrofuran / 2 h / Heating

1.3: 70 percent / aq. H₂SO₄ / tetrahydrofuran / 10 h

2.1: Mg; methanol

3.1: LiAlH₄ / tetrahydrofuran

4.1: O₃ / CH₂Cl₂; methanol / 0 °C

4.2: dimethylsulfide / CH₂Cl₂; methanol

5.1: trimethylorthoformate; p-TsOH

6.1: Et₃N; DMAP / CH₂Cl₂

7.1: NaH / dimethylsulfoxide

7.2: dimethylsulfoxide; tetrahydrofuran

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

9.1: aq. pyridinium p-toluenesulfonate / Heating

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

(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

((1S,2R,3R,6S)-3-Isopropenyl-2,6-dimethyl-cyclohexyl)-acetic acid ethyl ester

Downstream raw materials:

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

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

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

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