(1R,1R)-1-(1,5-dimethyl-1-hydroxy-4-hexene)-4-methyl-3-cyclohexenecarboxylic acid

Base Information

Chemical Name:(1R*,1R*)-1-(1,5-dimethyl-1-hydroxy-4-hexene)-4-methyl-3-cyclohexenecarboxylic acid
CAS No.:94294-81-2
Molecular Formula:C₁₆H₂₆O₃
Molecular Weight:266.381
Hs Code.:

Synonyms:(1R*,1R*)-1-(1,5-dimethyl-1-hydroxy-4-hexene)-4-methyl-3-cyclohexenecarboxylic acid

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Chemical Property of (1R*,1R*)-1-(1,5-dimethyl-1-hydroxy-4-hexene)-4-methyl-3-cyclohexenecarboxylic acid

Chemical Property:

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Technology Process of (1R*,1R*)-1-(1,5-dimethyl-1-hydroxy-4-hexene)-4-methyl-3-cyclohexenecarboxylic acid

There total 1 articles about (1R*,1R*)-1-(1,5-dimethyl-1-hydroxy-4-hexene)-4-methyl-3-cyclohexenecarboxylic acid 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:

: 110-93-0,129085-68-3
6-Methyl-hept-5-en-2-on

: 4342-60-3
4-methylcyclohex-3-enecarboxylic acid

: 94294-81-2
(1R*,1R*)-1-(1,5-dimethyl-1-hydroxy-4-hexene)-4-methyl-3-cyclohexenecarboxylic acid

: 94294-79-8
(1S*,1R*)-1-(1,5-dimethyl-1-hydroxy-4-hexene)-4-methyl-3-cyclohexenecarboxylic acid

Guidance literature:: With lithium diisopropyl amide; In tetrahydrofuran; at -40 ℃; for 1.5h; Yield given. Yields of byproduct given;
DOI:10.1021/ja00284a052

Reference yield:

: 94294-81-2
(1R*,1R*)-1-(1,5-dimethyl-1-hydroxy-4-hexene)-4-methyl-3-cyclohexenecarboxylic acid

: 94294-75-4,94294-76-5,104714-03-6,104757-61-1
4-[1,5-Dimethyl-hex-4-en-(E)-ylidene]-1-methyl-cyclohexane-1,2-diol

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

Reference yield:

: 94294-81-2
(1R*,1R*)-1-(1,5-dimethyl-1-hydroxy-4-hexene)-4-methyl-3-cyclohexenecarboxylic acid

: 94294-77-6,94294-78-7
Toluene-4-sulfonic acid (1S,2S)-5-[1,5-dimethyl-hex-4-en-(E)-ylidene]-2-hydroxy-2-methyl-cyclohexyl ester

Guidance literature:: Multi-step reaction with 10 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

10: pyr. / 10 h / 25 °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