(R)-1-[2-(2-methyl-1,4-cyclohexadienyl)ethyl]cyclohexa-2,4-dienecarboxylic acid

Base Information

Chemical Name:(R)-1-[2-(2-methyl-1,4-cyclohexadienyl)ethyl]cyclohexa-2,4-dienecarboxylic acid
CAS No.:199286-39-0
Molecular Formula:C₁₆H₂₀O₂
Molecular Weight:244.334
Hs Code.:

Synonyms:(R)-1-[2-(2-methyl-1,4-cyclohexadienyl)ethyl]cyclohexa-2,4-dienecarboxylic acid

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Chemical Property of (R)-1-[2-(2-methyl-1,4-cyclohexadienyl)ethyl]cyclohexa-2,4-dienecarboxylic acid

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Technology Process of (R)-1-[2-(2-methyl-1,4-cyclohexadienyl)ethyl]cyclohexa-2,4-dienecarboxylic acid

There total 5 articles about (R)-1-[2-(2-methyl-1,4-cyclohexadienyl)ethyl]cyclohexa-2,4-dienecarboxylic 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: 71.0%

: (1S,5S)-1-[2-(2-methyl-1,4-cyclohexadienyl)ethyl]-6-oxa-7-oxobicyclo[3.2.1]oct-3-ene

: 199286-39-0
(R)-1-[2-(2-methyl-1,4-cyclohexadienyl)ethyl]cyclohexa-2,4-dienecarboxylic acid

Guidance literature:: With potassium hexamethylsilazane; In tetrahydrofuran; at -30 ℃; for 4h;
DOI:10.1021/ja973034o

Reference yield:

: 199286-35-6
(R)-1-[2-(2-methyl-1,4-cyclohexadienyl)ethyl]-3-cyclohexenecarboxylic acid

: 199286-39-0
(R)-1-[2-(2-methyl-1,4-cyclohexadienyl)ethyl]cyclohexa-2,4-dienecarboxylic acid

Guidance literature:: Multi-step reaction with 3 steps

1: 79 percent / NaHCO₃, KI, I₂ / tetrahydrofuran; H₂O / 3 h / 23 °C

2: 96 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / benzene / 4 h / Heating

3: 71 percent / KHMDS / tetrahydrofuran / 4 h / -30 °C

With iodine; potassium hexamethylsilazane; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; potassium iodide; In tetrahydrofuran; water; benzene;
DOI:10.1021/ja973034o

Reference yield:

: 199286-34-5
(R)-3-[2-(2-Methyl-cyclohexa-1,4-dienyl)-ethyl]-6-vinyl-tetrahydro-pyran-2-one

: 199286-39-0
(R)-1-[2-(2-methyl-1,4-cyclohexadienyl)ethyl]cyclohexa-2,4-dienecarboxylic acid

Guidance literature:: Multi-step reaction with 5 steps

1: Et₃N / CH₂Cl₂ / 0.5 h / -78 - 23 °C

2: 2.) aq. LiOH / 1.) toluene, reflux, 4.5 h, 2.) THF, 23 deg C, 15 min

3: 79 percent / NaHCO₃, KI, I₂ / tetrahydrofuran; H₂O / 3 h / 23 °C

4: 96 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / benzene / 4 h / Heating

5: 71 percent / KHMDS / tetrahydrofuran / 4 h / -30 °C

With lithium hydroxide; iodine; potassium hexamethylsilazane; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; potassium iodide; In tetrahydrofuran; dichloromethane; water; benzene;
DOI:10.1021/ja973034o