m-Chloroperbenzoic acid → HCID 53697930, compound
Reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[F:12][C:13]1[CH:21]=[C:20]2[C:16]([C:17]([CH2:33][C:34]([OH:36])=[O:35])=[C:18]([CH3:32])[C:19]2=[CH:22][C:23]2[CH:28]=[CH:27][C:26]([S:29]([CH3:31])=[O:30])=[CH:25][CH:24]=2)=[CH:15][C:14]=1[O:37][CH3:38]>CC(C)=O>[F:12][C:13]1[CH:21]=[C:20]2[C:16]([C:17]([CH2:33][C:34]([OH:36])=[O:35])=[C:18]([CH3:32])[C:19]2=[CH:22][C:23]2[CH:28]=[CH:27][C:26]([S:29]([CH3:31])(=[O:9])=[O:30])=[CH:25][CH:24]=2)=[CH:15][C:14]=1[O:37][CH3:38]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of sodium periodate, 4.28 g (20 mol) in 40 ml of water is added dropwise to 6-fluoro-5-methoxy-2-methyl-1-(p-methylthiobenzylidene)-3-indenylacetic acid, 3.70 g (10 mmol) in 300 ml methanol and enough acetone to cause solution. This solution is stirred overnight at room temperature and filtered. The filtrate is evaporated at 30° to a small volume which causes the product to precipitate. The suspension is diluted with several volumes of water, and is cooled. Collected crystals are washed with water and methanol-water (1:1). The product is dried in vacuo over potassium hydroxide pellets and then in a vacuum oven at 70° C. The crude product is recrystallized from methylene chloride-petroleum ether to give 6-fluoro-5-methoxy-2-methyl-1-(p-methylsulfinyl-benzylidene)-3-indenylacetic acid (m.p. 190°-193°). 6-fluoro-5-methoxy-2-methyl-1-(p-methylsulfonylbenzylidene)-3-indenylacetic acid is prepared according to the procedure of Example 1, part G by the addition of 1.0 mol of m-chloroperbenzoic acid per mol of 6-fluoro-5-methoxy-2-methyl-1-(p-methylsulfinylbenzylidene)-3-indenyl acetic acid in an acetone solution.
Sources & evidence
- ORD record
- ord-c1d498c796e4498db680953814ad8263
- Source dataset
- uspto-grants-1997_12
- Patent number
- US05696159
Reaction notes
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