Hydrochloric Acid → p-Toluenesulfonic acid
Reaction equation
[H][H].[C:3]1([CH3:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(O)C.Cl.[S:14](=O)(=[O:17])([OH:16])[OH:15]>[Ni].[Pd].C(O)=O>[C:3]1([CH3:9])[CH:8]=[CH:7][C:6]([S:14]([OH:17])(=[O:16])=[O:15])=[CH:5][CH:4]=1Participants
Procedure
That is to say, 2-(1,3-dioxane-2-yl)ethyltriphenylphosphonium halide 12 and an aldehyde derivative 11 are subjected to a Wittig reaction in the presence of a base such as sodium methylate, potassium-t-butoxide (t-BuOK) or butyl lithium in an ether solvent such as tetrahydrofuran (abbreviated to as “THF”) or diethyl ether to obtain a compound 13. Next, the hydrogen reduction of the compound 13 is carried out in the presence of a metal catalyst such as palladium/carbon or a Raney nickel in a mixed solvent of toluene/ethanol, and the thus reduced compound is then reacted with a mineral acid such as hydrochloric acid or sulfuric acid, or an organic acid such as formic acid or p-toluenesulfonic acid to obtain an aldehyde derivative 14. Furthermore, this aldehyde derivative 14 and a compound 15 are subjected to the Wittig reaction in the same manner as in the above preparation of the compound 13 from the aldehyde derivative 11 to obtain a compound 16, and this compound is then reacted with the same acid as mentioned above, thereby preparing an aldehyde derivative 17. Next, this aldehyde derivative 17 is reacted with a Grignard reagent 18 to carry out a Grignard reaction, and the same acid as mentioned above is added to the reaction system to accomplish dehydration. In succession, the hydrogen reduction is done by the use of the same metal catalyst as mentioned above, whereby a derivative 19 having a butylene group can be manufactured.
Sources & evidence
- ORD record
- ord-097bbe1100b14d929ea6483435625286
- Source dataset
- uspto-grants-2001_01
- Patent number
- US06174459B1
Reaction notes
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