Ethanol → Ethyl 2-[4-(2-methylpropyl)phenyl]propanoate
Reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:15])[C:12]([OH:14])=[O:13])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].OS(O)(=O)=O.[CH2:21](O)[CH3:22]>>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]([CH3:15])[C:12]([O:14][CH2:21][CH3:22])=[O:13])=[CH:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3]Participants
Procedure
Separately, 72.02g ethyl 2-(4-isobutylphenyl)-propionate, obtained by the esterification of 2-(4-isobutylphenyl)-propionic acid with ethanol and concentrated H2SO4, are solved with 100ml methanol, this solution is introduced drop by drop into the reaction flask, and stirred and cooled for 5 hours on an ice bath. Thereafter it is suction filtered, the residue is washed with alltogether 50ml methanol, the wash is added to the filtrate, thereafter the whole is evaporated in a water bath with a rotating evaporator at a reduced pressure, until 100-200 ml of a concentrated solution are obtained. This solution is poured into a 200 ml beaker into which are stirred approximately 1000 ml 1,25N acetic acid. This mixture is left standing for 24 hours, thereafter suction filtered. The resulting filtrate is taken up with 100ml. petroleum ether at 40°-60° C, in order to solve any possible residue of unreacted starting ester, and refiltered. Approximately 50g of 2-(4-isobutylphenyl)-propriohydroxamic acid are obtained, having a melting point of 119°-121° C on Kofler's hot stage.
Sources & evidence
- ORD record
- ord-237896f456184d848013227b3fe3c78c
- Source dataset
- uspto-grants-1978_04
- Patent number
- US04082707
Reaction notes
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