(1S,2S,3R)-2-(2-Hydroxyethyl)-1,3-dimethyl-3-vinylcyclohexanol

Base Information

• Chemical Name: (1S,2S,3R)-2-(2-Hydroxyethyl)-1,3-dimethyl-3-vinylcyclohexanol
• CAS No.: 146383-55-3
• Molecular Formula: C₁₂H₂₂O₂
• Molecular Weight: 198.305
• Mol file: 146383-55-3.mol

Synonyms:(1S,2S,3R)-2-(2-Hydroxyethyl)-1,3-dimethyl-3-vinylcyclohexanol

Chemical Property of (1S,2S,3R)-2-(2-Hydroxyethyl)-1,3-dimethyl-3-vinylcyclohexanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,3R)-2-(2-Hydroxyethyl)-1,3-dimethyl-3-vinylcyclohexanol

There total 24 articles about (1S,2S,3R)-2-(2-Hydroxyethyl)-1,3-dimethyl-3-vinylcyclohexanol 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: 57.0%

(3R/S,4S,5R)-5-Methyl-4-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-5-vinyl-1-oxaspiro<2.5>octane (146383-54-2) → (1R,2S,3R)-2-(2-Hydroxyethyl)-1,3-dimethyl-3-vinylcyclohexanol (146451-39-0) + (1S,2S,3R)-2-(2-Hydroxyethyl)-1,3-dimethyl-3-vinylcyclohexanol (146383-55-3)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; Heating;

DOI:10.1016/S0040-4039(00)74773-3

Reference yield:

(2'S,3aS,3'R,4'R,5'R,7aR)-2'-(Hydroxymethyl)-4',5'-(isopropylidenedioxy)spiro-2(3H)-one → (1S,2S,3R)-2-(2-Hydroxyethyl)-1,3-dimethyl-3-vinylcyclohexanol (146383-55-3)

Guidance literature:

Multi-step reaction with 12 steps

1: 89 percent / NaH / dimethylformamide / 2 h / Ambient temperature

2: 77 percent / 60percent aq. TFA / 72 h / 5 °C

3: aq. NaIO₄ / methanol / 4 h / Ambient temperature

4: conc. aq. HCl / 72 h / -15 °C

5: 52 percent / Raney nickel T-4 / ethanol / 13 h / Heating

6: aq. NaIO₄ / methanol / 1 h / Ambient temperature

7: tetrahydrofuran / 0.17 h / Ambient temperature

8: 100 percent / LiAlH₄ / tetrahydrofuran / 0.33 h / Ambient temperature

9: 1.) imidazole, 2.) PCC, molecular sieves / 1.) DMF, r.t., 1 h, 2.) CH₂Cl₂, r.t., 1 h

10: tetrahydrofuran

11: 57 percent / m-CPBA, NaHCO₃ / CH₂Cl₂ / 21 h / 0 °C

12: 57 percent / LiAlH₄ / tetrahydrofuran / 1 h / Heating

With 1H-imidazole; hydrogenchloride; sodium periodate; lithium aluminium tetrahydride; molecular sieve; Raney nickel T-4; sodium hydride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; trifluoroacetic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00075a021

Reference yield:

(2'S,3aS,3'R,4'R,5'R,7aR)-2'-<(Benzyloxy)methyl>-4',5'-(isopropylidenedioxy)spiro-2(3H)-one → (1S,2S,3R)-2-(2-Hydroxyethyl)-1,3-dimethyl-3-vinylcyclohexanol (146383-55-3)

Guidance literature:

Multi-step reaction with 11 steps

1: 77 percent / 60percent aq. TFA / 72 h / 5 °C

2: aq. NaIO₄ / methanol / 4 h / Ambient temperature

3: conc. aq. HCl / 72 h / -15 °C

4: 52 percent / Raney nickel T-4 / ethanol / 13 h / Heating

5: aq. NaIO₄ / methanol / 1 h / Ambient temperature

6: tetrahydrofuran / 0.17 h / Ambient temperature

7: 100 percent / LiAlH₄ / tetrahydrofuran / 0.33 h / Ambient temperature

8: 1.) imidazole, 2.) PCC, molecular sieves / 1.) DMF, r.t., 1 h, 2.) CH₂Cl₂, r.t., 1 h

9: tetrahydrofuran

10: 57 percent / m-CPBA, NaHCO₃ / CH₂Cl₂ / 21 h / 0 °C

11: 57 percent / LiAlH₄ / tetrahydrofuran / 1 h / Heating

With 1H-imidazole; hydrogenchloride; sodium periodate; lithium aluminium tetrahydride; molecular sieve; Raney nickel T-4; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; trifluoroacetic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane;

DOI:10.1021/jo00075a021

upstream raw materials:

(3R/S,4S,5R)-5-Methyl-4-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-5-vinyl-1-oxaspiro<2.5>octane

(1R,2S,3R)-2-(2-Hydroxyethyl)-3-methyl-3-vinylcyclohexanol

(3aS,4R,7aR)-4-Methyl-4-vinylhexahydrobenzofuran-2(3H)-one

(3aS,4S,7aR)-4-Methyl-2-oxo-octahydro-benzofuran-4-carbaldehyde