Oxalyl chloride → 3-Chloro-2-(2-tetrahydrothienyl)-5,5-dimethyl-2-cyclohexen-1-one
Reaction equation
[S:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[C:6]1[C:7](=[O:15])[CH2:8][C:9]([CH3:14])([CH3:13])[CH2:10][C:11]=1O.C(Cl)(=O)C([Cl:19])=O>>[Cl:19][C:11]1[CH2:10][C:9]([CH3:14])([CH3:13])[CH2:8][C:7](=[O:15])[C:6]=1[CH:2]1[CH2:3][CH2:4][CH2:5][S:1]1Participants
Procedure
3 parts of 2-(2-tetrahydrothienyl)-3-hydroxy-5,5-dimethyl-2-cyclohexen-1-one was added to 9.9 parts of oxalic chloride, the mixture was stirred at room temperature for 1.5 hours and concentrated at a temperature below 50° C. The residue was dissolved in 40 parts by volume of benzene and 1.0 part of pyrolidine was added thereto. After stirring at room temperature for 1 hour, the mixture was washed with water, a saturated aqueous sodium hydrogen carbonate solution, and a saturated aqueous sodium chloride solution, in the order listed, and then dried. Benzene was distilled off and the residue was passed through a column containing silica gel using a solvent mixture of chloroform and benzene (2:1) as a spreading agent to obtain 1.1 parts of 3-chloro-2-(2-tetrahydrothienyl)-5,5-dimethyl-2-cyclohexen-1-one as a brown colored oily product.
Workup
- concentrationconcentrated at a temperature below 50° C
- dissolutionThe residue was dissolved in 40 parts by volume of benzene and 1.0 part of pyrolidine
- additionwas added
- stirringAfter stirring at room temperature for 1 hour
- washthe mixture was washed with water
- customdried
- distillationBenzene was distilled off
- additioncontaining silica gel using
- additiona solvent mixture of chloroform and benzene (2:1) as a spreading agent
Sources & evidence
- ORD record
- ord-c9734379535d406dba9afa290896ca49
- Source dataset
- uspto-grants-1982_06
- Patent number
- US04334010
Reaction notes
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