(1R,3R,4S)-p-menth-3-yl(S)-2-hydroxy-4-methoxy-6-methyl-1,3-cyclohexadiene-1-carboxylate, trifluoromethanesulfonate

Base Information

Chemical Name:(1R,3R,4S)-p-menth-3-yl(S)-2-hydroxy-4-methoxy-6-methyl-1,3-cyclohexadiene-1-carboxylate, trifluoromethanesulfonate
CAS No.:158818-67-8
Molecular Formula:C₂₀H₂₉F₃O₆S
Molecular Weight:454.508
Hs Code.:

Synonyms:(1R,3R,4S)-p-menth-3-yl(S)-2-hydroxy-4-methoxy-6-methyl-1,3-cyclohexadiene-1-carboxylate, trifluoromethanesulfonate

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Chemical Property of (1R,3R,4S)-p-menth-3-yl(S)-2-hydroxy-4-methoxy-6-methyl-1,3-cyclohexadiene-1-carboxylate, trifluoromethanesulfonate

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Technology Process of (1R,3R,4S)-p-menth-3-yl(S)-2-hydroxy-4-methoxy-6-methyl-1,3-cyclohexadiene-1-carboxylate, trifluoromethanesulfonate

There total 5 articles about (1R,3R,4S)-p-menth-3-yl(S)-2-hydroxy-4-methoxy-6-methyl-1,3-cyclohexadiene-1-carboxylate, trifluoromethanesulfonate 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: 95.0%

: 358-23-6
trifluoromethylsulfonic anhydride

: 158818-66-7
(1R,6S)-4-Methoxy-6-methyl-2-oxo-cyclohex-3-enecarboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

: 158818-67-8
(1R,3R,4S)-p-menth-3-yl(S)-2-hydroxy-4-methoxy-6-methyl-1,3-cyclohexadiene-1-carboxylate, trifluoromethanesulfonate

Guidance literature:: With sodium hydride; In diethyl ether; at -78 ℃;
DOI:10.1021/ja00104a041

Reference yield: 95.0%

: (1R,3R,4S)-p-menth-3-yl(1R,6S)-4-methoxy-6-methyl-2-oxo-3-cyclohexene-1-carboxylate

: 158818-67-8
(1R,3R,4S)-p-menth-3-yl(S)-2-hydroxy-4-methoxy-6-methyl-1,3-cyclohexadiene-1-carboxylate, trifluoromethanesulfonate

Guidance literature:: With trifluoromethanesulfonic acid anhydride; In disodium hydrogenphosphate; potassium dihydrogen phosphate;

Reference yield:

: 2216-51-5
(-)-menthol

: 158818-67-8
(1R,3R,4S)-p-menth-3-yl(S)-2-hydroxy-4-methoxy-6-methyl-1,3-cyclohexadiene-1-carboxylate, trifluoromethanesulfonate

Guidance literature:: Multi-step reaction with 4 steps

1: 95 percent / toluene / 26 h / Heating

2: 36 percent / KOt-Bu / 2-methyl-propan-2-ol / reflux, 2.5 h, rt

3: 71 percent / camphorsulfonic acid / 12 h / 23 °C

4: 1.) NaH / 1.) Et₂O, 0 deg C to 23 deg C, 5 h, 2.) -78 deg C to 0 deg C, 40 min

With camphor-10-sulfonic acid; potassium tert-butylate; sodium hydride; In toluene; tert-butyl alcohol;
DOI:10.1021/ja9703741