Hydrochloric Acid → 6-(3-Chloro-2-oxopropyl)-2,2-dimethyl-2H,4H-1,3-dioxin-4-one

HRID 486840Notes

Reaction equation

HRID 486840 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]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6577Chloroacetyl chlorideHCID 793682,2,6-Trimethyl-4H-1,3-dioxin-4-oneHCID 2724682Lithium diisopropylamide

Product 1

HCID 149448286-(3-Chloro-2-oxopropyl)-2,2-dimethyl-2H,4H-1,3-dioxin-4-oneYield 69%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8857Ethyl AcetateSolvent

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

  1. customwas gradually returned to room temperature
  2. extractionthe solution, and extraction
  3. dry with materialThe resultant organic layer was dried over anhydrous magnesium sulfate
  4. distillationNext, the solvent was distilled off

Sources & evidence

ORD record
ord-a65d247b196c473c9f4225b28a2ea62e
Source dataset
uspto-grants-1994_03
Patent number
US05292891

Reaction notes

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