4-Hydroxy-2,2,6-trimethylcyclohexanone

Base Information

• Chemical Name: 4-Hydroxy-2,2,6-trimethylcyclohexanone
• CAS No.: 20548-02-1
• Molecular Formula: C9H16O2
• Molecular Weight: 156.225
• UNII: X5GI5QTU0I
• DSSTox Substance ID: DTXSID10558901
• Nikkaji Number: J662.804D
• Mol file: 20548-02-1.mol

Synonyms:20548-02-1;4-hydroxy-2,2,6-trimethylcyclohexanone;4-hydroxy-2,2,6-trimethylcyclohexan-1-one;Cyclohexanone, 4-hydroxy-2,2,6-trimethyl-;X5GI5QTU0I;UNII-X5GI5QTU0I;SCHEMBL960112;DTXSID10558901;CSPVUHYZUZZRGF-UHFFFAOYSA-N;NS00006687;EN300-267571;G52713

Chemical Property of 4-Hydroxy-2,2,6-trimethylcyclohexanone

Chemical Property:

• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 156.115029749
• Heavy Atom Count: 11
• Complexity: 172

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC(CC(C1=O)(C)C)O

Technology Process of 4-Hydroxy-2,2,6-trimethylcyclohexanone

There total 19 articles about 4-Hydroxy-2,2,6-trimethylcyclohexanone 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: 98.1%

2,6,6-trimethyl-2-cyclohexene-1,4-dione (1125-21-9) → trans (4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexanone (20548-02-1)

Guidance literature:

With hydrogen; Ra-Ni; In methanol; at 25 ℃; for 8h; under 825.07 Torr;

DOI:10.1002/hlca.19890720223

Reference yield: 84.0%

2,6,6-trimethyl-2-cyclohexene-1,4-dione (1125-21-9) → trans (4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexanone (20548-02-1) + (4S)-4-hydroxy-2,6,6-trimethyl-cyclohex-2-en-one (64809-50-3) + (+)-(R)-4-Hydroxy-2,6,6-trimethyl-2-cyclohexen-1-one (76686-09-4) + 4-hydroxy-3,5,5-trimethyl-2-cyclohexen-1-one

Guidance literature:

With sodium hydroxide; (R_Ru)-[RuCl((S,R)-ADPE^-1)(η⁶-p-cymene)]; isopropyl alcohol; at 28 ℃; for 1h;

DOI:10.1016/S0957-4166(00)00141-5

Reference yield: 83.0%

(6R)-levodione (60046-49-3) → (4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexan-1-one (20548-02-1,55058-51-0,60686-81-9,60686-82-0,82977-53-5,90082-06-7,90129-05-8,99881-84-2,60046-50-6)

Guidance literature:

With hydrogen; Raney-Ni (W₂-activity); In methanol; for 1h;

DOI:10.1021/np970517x

upstream raw materials:

2,6,6-trimethyl-2-cyclohexene-1,4-dione

(6R)-levodione

2,6,6-trimethyl-1,4-cyclohexanedione

triisobutylaluminum

Downstream raw materials:

1-ethynyl-1,4-dihydroxy-2,2,6-trimethyl-cyclohexane

(1R,4R,6S)-1-<(E)-5-hydroxy-3-methylpent-3-en-1-ynyl>-2,2,6-trimethylcyclohexane-1,4-diol

(+)-(4R,6S)-4-hydroxy-2,2,6-trimethylcyclohexanone

desoxy-mytiloxanthin