Thionyl Chloride → Heptylbenzoyl chloride
Reaction equation
[CH2:1]([C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10](O)=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].O=S(Cl)[Cl:19]>>[CH2:1]([C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([Cl:19])=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]Participants
3
Procedure
Heptylbenzoyl chloride (530 mg., 0.0022 M), obtained by reaction of heptylbenzoic acid with SOCl2, and 380 mg. of ##STR15## (0.002 M) in 5 ml. of pyridine are allowed to react at ambient temperature for 48 hours. Then the reaction mixture is poured into a solution of 5 ml. of concentrated H2SO4 and 50 g. of ice. The organic fraction is extracted with ether (3 times, 100 ml. total). The organic fraction is washed with water (3 times) and dried over anhydrous Na2SO4. The solvent is evaporated and the solid residue is treated by chromatography on silica with a benzene (50%) hexane (50%) mixture. The product is finally recrystallized twice from ethanol. The yield is above 80%.
Sources & evidence
- ORD record
- ord-d2d113151734485182f3aa6cb97be9e5
- Source dataset
- uspto-grants-1979_04
- Patent number
- US04147655
Reaction notes
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