Oct-7-en-1-ol → 7-Octenoic acid
Reaction equation
[CH2:1]([OH:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]=[CH2:8].CC(C)=[O:12].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[C:1]([OH:12])(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]=[CH2:8]Participants
4
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 152 g of oct-7-en-1-ol (prepared in Example 22 B-1) in 3.4 liters of acetone there was added 1.4 M of Jones Reagent (986 ml) while the mixture was maintained at less than 10° C. The mixture was stirred for 10 min and was quenched with 100 ml of isopropanol. The acetone volume was reduced in vacuo and the residue was diluted with water and extracted three times with equal volumes of ethyl acetate. The combined ethyl acetate extracts were washed two times with water, then with saturated aqueous sodium chloride, dried over magnesium sulfate and evaporated in vacuo to yield 164 g of the title compound having the following physical characteristics: