Hydrochloric Acid → 6-(3-Chloro-2-oxopropyl)-2,2-dimethyl-2H,4H-1,3-dioxin-4-one
Reaction equation
[CH3:1][C:2]1([CH3:10])[O:7][C:6](=[O:8])[CH:5]=[C:4]([CH3:9])[O:3]1.[Cl:11][CH2:12][C:13](Cl)=[O:14].[Li+].CC([N-]C(C)C)C.Cl>C(OCC)(=O)C.CCOCC>[CH3:1][C:2]1([CH3:10])[O:7][C:6](=[O:8])[CH:5]=[C:4]([CH2:9][C:13](=[O:14])[CH2:12][Cl:11])[O:3]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
In an argon gas stream, 20.6 ml of n-butyl lithium (1.6M solution in hexane) were added to 60 ml of an ether solution containing 3.53 g (0.033 mol) of diisopropylamine at -20° C. to form LDA. After stirring for 30 minutes, a mixture of 4.26 g (0.03 mol) of 2,2-dimethyl-6-methyl-1,3-dioxin-4-one and 60 ml of ether as well as 60 ml of an ether solution containing 1.69 g (0.015 mol) of chloroacetyl chloride were added to LDA. After the temperature was gradually returned to room temperature, 10% hydrochloric acid was added thereto to neutralize the solution, and extraction was then carried out with ether. The resultant organic layer was dried over anhydrous magnesium sulfate. Next, the solvent was distilled off, and the residue was then subjected to column chromatography (an eluent of hexane:ethyl acetate =4:1), thereby obtaining 2.26 g (yield 69%) of 2,2-dimethyl-6-(3-chloro-2-oxopropyl)-1, 3-dioxin-4 -one.
Workup
- customwas gradually returned to room temperature
- extractionthe solution, and extraction
- dry with materialThe resultant organic layer was dried over anhydrous magnesium sulfate
- distillationNext, the solvent was distilled off
Sources & evidence
- ORD record
- ord-869ba30ddd7c442d86a0c3d74ba9675d
- Source dataset
- uspto-grants-1993_10
- Patent number
- US05256800
Reaction notes
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