Diketene → HCID 131716806, compound
Reaction equation
[CH:1]([OH:6])([OH:5])[CH2:2][CH2:3][CH3:4].[CH2:7]=[C:8]1[O:12][C:10](=[O:11])[CH2:9]1>>[CH2:10]([OH:11])[CH2:9][CH:8]([OH:12])[CH3:7].[C:1]([O-:6])(=[O:5])[CH2:2][C:3]([CH3:4])=[O:11]Participants
3
Procedure
5 mmol of triethylamine are mixed with 1 mol of 1,3-butanediol. The mixture is kept on ice and stirred while 1 mol of diketene is added dropwise over 1.5 hours. Stirring is continued for 5 to 7 hours at 0° C., then for 15 hours at room temperature. The reaction is monitored occasionally by proton NMR and after 15 hours, it is complete. This procedure yields a mixture of butanediol-acetoacetate and butanediol-diacetoacetate in proportion 77:23 (assayed by gas chromatography). Butanediol-diacetoacetate can be obtained as a main product by reacting 1 mol of butanediol with 2 mol of diketene.
Sources & evidence
- ORD record
- ord-68a2302eeaac4bf08b6606384a166732
- Source dataset
- uspto-grants-1991_03
- Patent number
- US04997976
Reaction notes
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