Thionyl Chloride → HCID 178444542, compound
Reaction equation
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]([O:14]C2C=CC3C(=CC=C(C#N)C=3)C=2)=O)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].C([C@H]1CC[C@H](C(O)=O)CC1)CCCC.S(Cl)([Cl:43])=O>>[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]([Cl:43])=[O:14])[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5]Participants
Procedure
Preparation of 6-cyano-2-naphthyl trans-4-n-pentylcyclohexane-1-carboxylate by the following route: ##STR17## trans-4-n-Pentylcyclohexane-1-carboxylic acid chloride is prepared (step A9) by the standard procedure of heating a solution of trans-4-n-pentylcyclohexane-1-carboxylic acid (0.01 mole) in an excess of thionyl chloride for 2 hours. Removal of the excess of thionyl chloride gives a residue of the acid chloride which is mixed with dry pyridine (40 ml) and cooled to 0°-5° C. 6-Cyano-2-naphthol (0.012 mole), as prepared in Example 4 above, is then added and the solution stirred at room temperature for 20 hours; during this time the reaction mixture is protected from atmospheric moisture by a calcium chloride guard tube. The pyridine is then removed by rotary evaporation. The residual solid is purified by column chromatography on silica gel, using chloroform or chloroform:hexane (2:1) mixture as eluent. The purified ester is isolated and crystallised from hexane or methanol until constant transition temperatures are obtained: crystal-nematic liquid crystal (C-N); 86.5° C.; nematic liquid crystal-isotropic liquid (N-I), 168.3° C.
Workup
- customRemoval of the excess of thionyl chloride
Sources & evidence
- ORD record
- ord-3e931776cfff4b1eb42e878722ec902f
- Source dataset
- uspto-grants-1978_09
- Patent number
- US04113647
Reaction notes
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