Sodium Acetate → Methyl 5,8-dimethyl-4-hydroxy-1,1-dioxo-1,2,3,4-tetrahydro-1lambda6-thiochromene-6-carboxylate
Reaction equation
[CH3:1][C:2]1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][C:9]([CH3:16])=[C:8]2[C:3]=1[CH:4]([OH:17])[CH2:5][CH2:6]S2.C([O-])(=O)C.[Na+].O[O:24][S:25]([O-:27])=O.[K+].S([O-])(O[O-])(=O)=O.[K+].[K+]>O.CO>[CH3:1][C:2]1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][C:9]([CH3:16])=[C:8]2[C:3]=1[CH:4]([OH:17])[CH2:5][CH2:6][S:25]2(=[O:27])=[O:24]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
10 g (0.04 mol) of methyl 5,8-dimethyl-4-hydroxy-6-thiochromanecarboxylate and 4.9 g (0.06 mol) of sodium acetate were together added to 200 ml of methanol. The mixture was cooled to 0° C. and slowly admixed with a solution of 41.4 g (0.07 mol) of OXONE® (potassium peroxymonosulfate) in 200 ml of water. During the addition, the reaction temperature was kept below 6° C. The mixture was subsequently stirred at room temperature for 4 h and then diluted with 120 ml of water. The mixture was extracted with methylene chloride (3×200 ml), and the extract was dried over MgSO4 and concentrated using a rotary evaporator.
Workup
- additionDuring the addition
- customwas kept below 6° C
- extractionThe mixture was extracted with methylene chloride (3×200 ml)
- dry with materialthe extract was dried over MgSO4
- concentrationconcentrated
- customa rotary evaporator
Sources & evidence
- ORD record
- ord-0065794afdaa4cfe8aed8981e206ab06
- Source dataset
- uspto-grants-2001_10
- Patent number
- US06297196B1
Reaction notes
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