Oxalyl chloride → HCID 13923222, compound
Reaction equation
[C:1]([Cl:6])(=O)[C:2](Cl)=O.[C:7]([C:12]1[C:13](=[O:25])[CH2:14][CH:15]([CH:19]2[CH2:24][CH2:23][CH2:22][S:21][CH2:20]2)CC=1O)(=[O:11])[CH2:8][CH2:9][CH3:10]>C(OC)(C)(C)C>[C:7]([C:12]1[C:13](=[O:25])[CH2:14][CH:15]([CH:19]2[CH2:24][CH2:23][CH2:22][S:21][CH2:20]2)[CH2:2][C:1]=1[Cl:6])(=[O:11])[CH2:8][CH2:9][CH3:10]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
420 ml of oxalyl chloride were added at 0° to 5° C. to 141.2 g (0.5 mol) of 2-butyryl-3-hydroxy-5-(tetrahydrothiopyran-3-yl)cyclohex-2-en-1-one, and the mixture was stirred at room temperature for 16 hours and concentrated. The oil obtained was treated with methyl tert.-butyl ether, and the resulting solid was filtered off with suction and dried. This gave 125.9 g (84% yield) of 2-butyryl-3-chloro-5-(tetrahydrothiopyran-3-yl)cyclohex-2-en-1-one having a melting point of 97° C. (decomposition) (compound no. 312).