Methanol → HCID 86101757, compound
Reaction equation
[CH3:1][C:2]([CH2:9][CH3:10])=[CH:3][CH2:4][CH2:5][C:6](=[O:8])[CH3:7].S(=O)(=O)(O)O.[CH3:16][OH:17]>>[CH3:16][O:17][C:2]([CH3:1])([CH2:9][CH3:10])[CH2:3][CH2:4][CH2:5][C:6](=[O:8])[CH3:7]Participants
4
Procedure
To 2 kg 6-methyl-oct-5-en-2-one in 4 l methanol was added 800 ml concentrated sulphuric acid at 3° C. over a period of 40 minutes. After further stirring for 5 h at room temperature, the solution was poured onto 8 kg of ice water and extracted with tert.-butyl methyl ether. The combined organic phases were washed with 20% Na2CO3 (200 ml) and concentrated NaCl solution (3×150 ml). After removal of the solvent, the residue was distilled over a 70 cm Sulzer column to give 840 g recovered starting material (boiling point: 72°-75° C./10 mm Hg) and 970 g 6-methoxy-6-methyl-2-octanone (bp.: 95°-98° C./10 Torr=13.3 mbar).
Workup
- extractionextracted with tert.-butyl methyl ether
- washThe combined organic phases were washed with 20% Na2CO3 (200 ml) and concentrated NaCl solution (3×150 ml)
- customAfter removal of the solvent
- distillationthe residue was distilled over a 70 cm Sulzer column
- customto give 840 g
- customrecovered
Sources & evidence
- ORD record
- ord-858f63c0e7414177afe925ea08e4d3f7
- Source dataset
- uspto-grants-2010_09
- Patent number
- US07790668B2
Reaction notes
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