Water → 3-Formylbut-2-enyl acetate

To a solution of 4-acetoxy-2-methyl-2-buten-1-ol (6.69 g, 46.4 mmol) in dimethylformamide (40 ml) were added 2,2,6,6-tetramethyl-piperidine-1-oxy (0.39 g, 2.32 mmol, 5 mol %) and cuprous chloride (0.48 g, 4.64 mmol, 10 mol %). The mixture was subjected to reaction for 8 hours while bubbling oxygen at a rate of about 100 ml/min. After completion of the reaction, the reaction mixture was poured into ice-cooled water (30 ml) and extracted with ether (100 ml) three times. The extract was dried over anhydrous magnesium sulfate. Evaporation of the ether followed by purification by column chromatography (ethyl acetate-hexane (=1:3)) gave 4-acetoxy-2-methyl-2-buten-1-al (6.02 g, 42.3 mmol; Yield: 91.2%).

1. customThe mixture was subjected to reaction for 8 hours
2. customwhile bubbling oxygen at a rate of about 100 ml/min
3. customAfter completion of the reaction
4. additionthe reaction mixture was poured into ice-
5. extractionextracted with ether (100 ml) three times
6. dry with materialThe extract was dried over anhydrous magnesium sulfate
7. customEvaporation of the ether
8. customfollowed by purification by column chromatography (ethyl acetate-hexane (=1:3))

ORD record

ord-103d8784741446049982968a5a5bf106

Source dataset

uspto-grants-1995_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05424478