<1,2-trans,4(E)>-4-(1',5'-Dimethyl-4'-hexen-1'-yliden)-1-methyl-1,2-cyclohexandiol

Base Information

• Chemical Name: <1,2-trans,4(E)>-4-(1',5'-Dimethyl-4'-hexen-1'-yliden)-1-methyl-1,2-cyclohexandiol
• CAS No.: 94294-75-4
• Molecular Formula: C₁₅H₂₆O₂
• Molecular Weight: 238.37
• Mol file: 94294-75-4.mol

Synonyms:<1,2-trans,4(E)>-4-(1',5'-Dimethyl-4'-hexen-1'-yliden)-1-methyl-1,2-cyclohexandiol

Chemical Property of <1,2-trans,4(E)>-4-(1',5'-Dimethyl-4'-hexen-1'-yliden)-1-methyl-1,2-cyclohexandiol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <1,2-trans,4(E)>-4-(1',5'-Dimethyl-4'-hexen-1'-yliden)-1-methyl-1,2-cyclohexandiol

There total 16 articles about <1,2-trans,4(E)>-4-(1',5'-Dimethyl-4'-hexen-1'-yliden)-1-methyl-1,2-cyclohexandiol 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: 96.0%

(1S*,3R*,4S*,6S*)-6-acetoxy-4-chloro-1,3-dimethyl-3-(4-methyl-3-pentene)-2-oxabicyclo<2.2.2>octane (94294-74-3) → <1,2-trans,4(E)>-4-(1',5'-Dimethyl-4'-hexen-1'-yliden)-1-methyl-1,2-cyclohexandiol (94294-75-4)

Guidance literature:

With sodium; In diethyl ether; for 12h; Heating;

DOI:10.1021/ja00284a052

Reference yield:

Acetic acid (1S,3R,4S,6R)-4-chloro-1,3-dimethyl-3-(4-methyl-pent-3-enyl)-2-oxa-bicyclo[2.2.2]oct-6-yl ester (94294-74-3,94347-07-6,104713-99-7,104714-00-3) → 4-[1,5-Dimethyl-hex-4-en-(E)-ylidene]-1-methyl-cyclohexane-1,2-diol (94294-75-4,94294-76-5,104714-03-6,104757-61-1)

Guidance literature:

With sodium; ethylamine; In tetrahydrofuran; at 0 ℃; for 10h; Yield given;

DOI:10.1021/ja00288a048

Reference yield:

(1R*,1R*)-1-(1,5-dimethyl-1-hydroxy-4-hexene)-4-methyl-3-cyclohexenecarboxylic acid (94294-81-2) → 4-[1,5-Dimethyl-hex-4-en-(E)-ylidene]-1-methyl-cyclohexane-1,2-diol (94294-75-4,94294-76-5,104714-03-6,104757-61-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 97 percent / I₂ / CH₂Cl₂ / 1.) 0 deg C, 30 min; 2.) room temp., 30 min

2: 98 percent / KOH / tetrahydrofuran / 1.) 0 deg C, 30 min; 2.) 20 deg C, 1 h

3: 100 percent / p-TSA / CH₂Cl₂ / 0.17 h / 0 °C

4: pyr / 6 h / 25 °C

5: Br₂ / CCl₄ / 2 h

6: N-chlorosuccinimide/Pb(OAc)4 / dimethylformamide; acetic acid / 2 h / 40 - 50 °C

7: 94 percent / Zn/HOAc / diethyl ether / 4 h / 25 °C

8: pyr. / 10 h / 25 °C

9: sodium metal/EtNH₂ / tetrahydrofuran / 10 h / 0 °C

With pyridine; lead(IV) acetate; potassium hydroxide; N-chloro-succinimide; bromine; iodine; sodium; ethylamine; acetic acid; zinc; toluene-4-sulfonic acid; In tetrahydrofuran; tetrachloromethane; diethyl ether; dichloromethane; acetic acid; N,N-dimethyl-formamide;

DOI:10.1021/ja00288a048

upstream raw materials:

(1,2-trans)-4-<1',5'-Dimethyl-1'-(tetrahydro-2''-pyranyloxy)-4'-hexen-1'-yl>-1-methyl-2-(tetrahydro-2'''-pyranyloxy)-4-cyclohexen-1-ol

(1S*,3R*,4S*,6S*)-6-acetoxy-4-chloro-1,3-dimethyl-3-(4-methyl-3-pentene)-2-oxabicyclo<2.2.2>octane

1-<(4,5-trans)-4,5-Dihydroxy-4-methyl-1-cyclohexen-1-yl>ethanon

1-<(4,5-trans)-4-Hydroxy-4-methyl-5-(tetrahydro-2-pyranyloxy)-1-cyclohexen-1-yl>ethanon

Downstream raw materials:

Toluene-4-sulfonic acid (1S,2S)-5-[1,5-dimethyl-hex-4-en-(E)-ylidene]-2-hydroxy-2-methyl-cyclohexyl ester

(1S*,2S*)-2-bromo-1-methyl-4-((E)-1,5-dimethylhex-4-enylidene)cyclohexan1-ol

Methanesulfonic acid (1S,2S)-5-[1,5-dimethyl-hex-4-en-(E)-ylidene]-2-hydroxy-2-methyl-cyclohexyl ester