Methanol → Methyl 8-oxooctanoate
Reaction equation
[CH:1]1[CH2:8][CH2:7]CC[CH2:4][CH2:3][CH:2]=1.[C:9](=[O:12])(O)[O-:10].[Na+].Cl[CH2:15]Cl.C(N(CC)CC)C.[CH3:24][OH:25]>>[O:25]=[CH:24][CH2:7][CH2:8][CH2:1][CH2:2][CH2:3][CH2:4][C:9]([O:10][CH3:15])=[O:12]Participants
6
Procedure
48 g cyclooctene (1) and 8.4 g sodium bicarbonate were ozonolysed in 48 g methanol and 1 l dichloromethane at −78° C. for 5.5 h. 304 g triethylamine was added slowly dropwise at −60 [lacuna] C and the reaction mixture was allowed to warm to room temperature in the course of 1 h. The reaction mixture was washed with sodium thiosulphate solution (10%, 200 ml), 2 N HCl (150 ml), NaOH (5%, 150 ml) and NaCl solution (saturated, 200 ml) and dried over sodium sulphate and the solvent was distilled off. After distillation, methyl 8-oxooctanoate (2) was obtained.
Workup
- washThe reaction mixture was washed with sodium thiosulphate solution (10%, 200 ml), 2 N HCl (150 ml), NaOH (5%, 150 ml) and NaCl solution (saturated, 200 ml)
- dry with materialdried over sodium sulphate
- distillationthe solvent was distilled off
- distillationAfter distillation
Sources & evidence
- ORD record
- ord-42603ca4faa4454f83dbfb7edc008a5f
- Source dataset
- uspto-grants-2008_02
- Patent number
- US07332468B2
Reaction notes
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