Methanol → Phenyl(2-phenyl-4,7-dihydro-2H-1,3-dioxepin-2-yl)methanone
Reaction equation
CO.[C:3]1([C:9]([C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:12])=[O:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.S(Cl)(Cl)=O.[CH2:23](O)/[CH:24]=[CH:25]\[CH2:26][OH:27]>>[C:11]([C:9]1([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[O:27][CH2:26][CH:25]=[CH:24][CH2:23][O:10]1)(=[O:12])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1Participants
Procedure
60.8 g (1.9 mols) of methanol were added with stirring to a suspension of 105 g (0.5 mol) of benzil in 107.1 g (0.9 mol) of thionyl chloride, with cooling to a temperature below 10° C. The mixture was initially stirred until room temperature was reached, and then it was stirred for 2 hours at 50° C. 52.8 g (0.6 mol) of cis-2-butene-1,4-diol were added to the clear, pale yellow solution, and volatile products were distilled off at 10 torr and 50° C. The mixture was then stirred for 3 hours at from 60° to 65° C. under normal pressure, 15 g of potassium carbonate and 200 ml of isopropanol were added, and the reaction product was precipitated by the dropwise addition of 100 ml of water. 110.4 g of 2-benzoyl-2-phenyl-4,7-dihydro-1,3-dioxepin were obtained, having a melting point of from 115° to 119° C. After recrystallizing from isopropanol, the melting point was from 118° to 119° C.
Workup
- temperaturewith cooling to a temperature below 10° C
- stirringit was stirred for 2 hours at 50° C
- distillationwere distilled off at 10 torr and 50° C
- stirringThe mixture was then stirred for 3 hours at from 60° to 65° C. under normal pressure, 15 g of potassium carbonate and 200 ml of isopropanol
- additionwere added
- customthe reaction product was precipitated by the dropwise addition of 100 ml of water
Sources & evidence
- ORD record
- ord-21dd5944b17840258a8a06b11c0531ec
- Source dataset
- uspto-grants-1984_11
- Patent number
- US04485249
Reaction notes
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