Sulfuric Acid → 3-Carboethoxy-2-cyano-2-hydroxy-3,5-dimethylcyclopentanone
Reaction equation
[OH-].[Na+].[C:3]([C:8]1([CH3:17])[CH2:12][CH:11]([CH3:13])[C:10](=[O:14])[CH:9]1[C:15]#[N:16])([O:5][CH2:6][CH3:7])=[O:4].[OH:18]OS([O-])=O.[K+].S(=O)(=O)(O)O>O>[C:3]([C:8]1([CH3:17])[CH2:12][CH:11]([CH3:13])[C:10](=[O:14])[C:9]1([C:15]#[N:16])[OH:18])([O:5][CH2:6][CH3:7])=[O:4]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
29.5 g (77.5 mmol) of borax and 24.8 g (0.62 mol) of sodium hydroxide are dissolved in 310 ml of water and treated while cooling (17° C.) with 65 g (310 mmol) of 3-carboethoxy-2-cyano-3,5-dimethylcyclopentanone (prepared from ethyl methacrylate and sodium cyanide according to H. Stetter et al, Liebig's Annalen d. Chem. 1979, 944-949). 132.2 g (403 mmol) of Caroat dissolved in 428 ml of water are added dropwise at 13° C. to 19° C. within 25 minutes and the mixture is stirred at room temperature for 3 hours. For the working-up, the mixture is acidified with 30 ml of sulphuric acid (2:1) and extracted four times with ethyl acetate. The organic phase is dried over sodium sulphate, concentrated and dried in a high vacuum for 2 hours. There are obtained 69.8 g (100%) of 3-carboethoxy-2-cyano-2-hydroxy-3,5-dimethylcyclopentanone in the form of a diestereomeric mixture: nD20 =1.4658.
Workup
- additiontreated
- additionare added dropwise at 13° C. to 19° C. within 25 minutes
- extractionextracted four times with ethyl acetate
- dry with materialThe organic phase is dried over sodium sulphate
- concentrationconcentrated
- customdried in a high vacuum for 2 hours
Sources & evidence
- ORD record
- ord-ddc16029704945f09400d74fa63b4e56
- Source dataset
- uspto-grants-1984_01
- Patent number
- US04428886
Reaction notes
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