(3R,4S)-4-hydroxy-3-methylcyclohexanone

Base Information

• Chemical Name: (3R,4S)-4-hydroxy-3-methylcyclohexanone
• CAS No.: 122090-90-8
• Molecular Formula: C₇H₁₂O₂
• Molecular Weight: 128.171
• Mol file: 122090-90-8.mol

Synonyms:(3R,4S)-4-hydroxy-3-methylcyclohexanone

Chemical Property of (3R,4S)-4-hydroxy-3-methylcyclohexanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S)-4-hydroxy-3-methylcyclohexanone

There total 7 articles about (3R,4S)-4-hydroxy-3-methylcyclohexanone 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%

(1S,2R)-4,4-ethylenedioxy-2-methylcyclohexanol (122090-89-5) → (3R,4S)-4-hydroxy-3-methylcyclohexanone (122090-90-8,89897-04-1)

Guidance literature:

With Amberlite IR-120; In water; for 3h; Heating;

DOI:10.1016/S0040-4020(01)86136-6

Reference yield:

ethyl 8-oxo-1,4-dioxaspiro[4.5]decane-7-carboxylate (14160-65-7,77793-24-9,122090-88-4) → (3R,4S)-4-hydroxy-3-methylcyclohexanone (122090-90-8,89897-04-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 10 g / baker's yeast, sucrose / H₂O; ethanol / 30 °C

2: 4-N,N-dimethylaminopyridine / pyridine / Ambient temperature

3: 95 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

4: 87 percent / p-TsOH / CH₂Cl₂ / 3 h / Ambient temperature

5: 83 percent / NBS / AIBN / benzene / 1 h / 50 °C

6: 83 percent / LiAlH₄ / tetrahydrofuran / Ambient temperature

7: 99 percent / Amberlite IR-120 / H₂O / 3 h / Heating

With N-Bromosuccinimide; lithium aluminium tetrahydride; baker's yeast; Amberlite IR-120; Sucrose; dmap; 2,2'-azobis(isobutyronitrile); toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; ethanol; dichloromethane; water; benzene;

DOI:10.1016/S0040-4020(01)86136-6

Reference yield:

(1S,2S)-4,4-ethylenedioxy-2-hydroxymethylcyclohexanol (96894-00-7) → (3R,4S)-4-hydroxy-3-methylcyclohexanone (122090-90-8,89897-04-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 87 percent / p-TsOH / CH₂Cl₂ / 3 h / Ambient temperature

2: 83 percent / NBS / AIBN / benzene / 1 h / 50 °C

3: 83 percent / LiAlH₄ / tetrahydrofuran / Ambient temperature

4: 99 percent / Amberlite IR-120 / H₂O / 3 h / Heating

With N-Bromosuccinimide; lithium aluminium tetrahydride; Amberlite IR-120; 2,2'-azobis(isobutyronitrile); toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; water; benzene;

DOI:10.1016/S0040-4020(01)86136-6

upstream raw materials:

(1S,2R)-4,4-ethylenedioxy-2-methylcyclohexanol

ethyl 8-oxo-1,4-dioxaspiro[4.5]decane-7-carboxylate

(1S,2S)-4,4-ethylenedioxy-2-hydroxymethylcyclohexanol

(1R,2S)-5,5-(Ethylendioxy)-2-hydroxycyclohexancarbonsaeure-ethylester

Downstream raw materials:

(3R,4S)-3-methyl-4-tetrahydropyranyloxycyclohexanone

3-((1R,2R,3R)-3-Hydroxy-1,2-dimethyl-6-oxo-cyclohexyl)-propionic acid methyl ester

benzyl (1'R,2'R,3'S)-3-(6',6'-ethylenedioxy-3'-hydroxy-1',2'-dimethylcyclohexane)propanoate

benzyl (1'R,2'R)-3-(6',6'-ethylenedioxy-1',2'-dimethyl-3'-oxocyclohexane)propanoate

Refernces