2,2-Dimethyl-1,3-dioxane-4,6-dione → 5-(2-Chlorobenzoyl)-2,2-dimethyl-1,3-dioxane-4,6-dione
Reaction equation
[CH3:1][C:2]1([CH3:10])[O:7][C:6](=[O:8])[CH2:5][C:4](=[O:9])[O:3]1.[Cl:11][C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14](Cl)=[O:15]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Cl:11][C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14]([CH:5]1[C:6](=[O:8])[O:7][C:2]([CH3:10])([CH3:1])[O:3][C:4]1=[O:9])=[O:15]Participants
5
Procedure
A solution of 4-(dimethylamino)pyridine (33.96 g; 278 mmol) and 2,2-dimethyl-1,3-dioxane-4,6-dione (20.0 g, 139 mmol) in 50 mL of CH2Cl2 was cooled in an ice-salt bath to −10° C. A solution of 2-chlorobenzoyl chloride (29.2 g, 167 mmol) in 20 mL of CH2Cl2 was added dropwise via addition funnel over 1 h. After stirring cold for 1 h, the reaction was allowed to warm to rt and stirred for an additional 3 h. The resulting yellow-orange solution was then extracted with an aq. 10% HCl solution (200 mL) and 200 mL of brine. After drying with MgSO4, the mixture was filtered and the solvent was removed in vacuo. The resulting orange oil was triturated with hexanes (3×50 mL), affording the title compound (20 g) as a yellow solid.
Workup
- stirringstirred for an additional 3 h
- extractionThe resulting yellow-orange solution was then extracted with an aq. 10% HCl solution (200 mL) and 200 mL of brine
- dry with materialAfter drying with MgSO4
- filtrationthe mixture was filtered
- customthe solvent was removed in vacuo
- customThe resulting orange oil was triturated with hexanes (3×50 mL)
Sources & evidence
- ORD record
- ord-f28672abc23541b2a269a6ecaf150c30
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07825278B2
Reaction notes
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