Thionyl Chloride → HCID 178455771, compound
Reaction equation
[CH2:1]([C@H:3]1[CH2:8][CH2:7][C@H:6]([C@H:9]2[CH2:14][CH2:13][C@H:12]([C:15]([OH:17])=O)[CH2:11][CH2:10]2)[CH2:5][CH2:4]1)[CH3:2].S(Cl)([Cl:20])=O>>[CH2:1]([C@H:3]1[CH2:8][CH2:7][C@H:6]([C@H:9]2[CH2:14][CH2:13][C@H:12]([C:15]([Cl:20])=[O:17])[CH2:11][CH2:10]2)[CH2:5][CH2:4]1)[CH3:2]Participants
Conditions
- Temperature
- 50 °C
Procedure
Trans-4-(trans-4-ethylcyclohexyl)cyclohexanecarboxylic acid (2.4 g, 0.01 mol) and thionyl chloride (10 ml) were introduced into a flask and warmed to 50° C. to obtain a uniform reaction liquid in 3 hours, followed by distilling off excess thionyl chloride under reduced pressure to obtain as a remaining oily substance, trans-4-(trans-4-ethylcyclohexyl)cyclohexanecarboxylic acid chloride. This acid chloride was added to a solution obtained by dissolving 2,4-difluorophenol (1.3 g, 0.01 mol) in pyridine (10 ml), followed by adding dry toluene (100 ml), sufficiently shaking the mixture, allowing it to stand over night, pouring the reaction liquid into water, washing with 6N hydrochloric acid, then with 2N NaOH aqueous solution, washing with water till the aqueous layer became neutral, drying the toluene layer with anhydrous sodium sulfate, drying, distilling off toluene under reduced pressure and recrystallizing the remaining oily substance from ethanol to obtain the objective trans-4-(trans-4-ethylcyclohexyl)cyclohexanecarboxylic acid-2,4-difluorophenyl ester. Yield 2.1 g (60%). It had a C-N point (phase transition point) of 76.3°-76.7° C. and a N-I point of 151.7° C. C, N and I are defined as in Table 1.
Workup
- customto obtain
- customa uniform reaction liquid in 3 hours
- distillationby distilling off excess thionyl chloride under reduced pressure
Sources & evidence
- ORD record
- ord-53e8bd01ff9e43c4940e2ffcabd22566
- Source dataset
- uspto-grants-1985_10
- Patent number
- US04548731
Reaction notes
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