Reaction equation
[F:1][C:2]([F:9])([F:8])[C:3](=[CH2:7])[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH2:15]=[C:16]1[CH:23]2[CH2:24][CH:19]3[CH2:20][CH:21]([CH2:25][CH:17]1[CH2:18]3)[CH2:22]2.[OH-].[Na+]>C1(C)C=CC=CC=1>[F:1][C:2]([F:9])([F:8])[C:3](=[CH2:7])[C:4]([O:6][C:16]1([CH3:15])[CH:17]2[CH2:25][CH:21]3[CH2:20][CH:19]([CH2:24][CH:23]1[CH2:22]3)[CH2:18]2)=[O:5]Participants
Conditions
- Temperature
- 5 °C
Procedure
A 500 ml flask was flushed with nitrogen to displace the air with nitrogen, and was charged with 70.0 g (0.50 mol) of α-trifluoromethylacrylic acid (supplied from Tosoh F-tech Inc.), 1.0 g (10 mmol) of sulfuric acid and 100 g of toluene. Separately 88.8 g (0.60 mol) of 2-methyleneadamantane, prepared by the same procedures as described in Reference Example 1, was dissolved in 100 g of toluene. The obtained solution of 2-methyleneadamantane in toluene was dropwise added to the content in the flask over a period of about 3 hours, while the content was maintained at a reaction temperature of about 5° C. Then the content was stirred for 15 hours at the same temperature. After completion of the reaction, the residual catalyst was neutralized by adding 40.0 g (50 mmol) of a 5% aqueous sodium hydroxide solution, and the neutralized liquid was washed with an aqueous saturated sodium chloride solution. The thus-obtained organic phase was subjected to column chromatography, and further, analyzed by NMR and mass spectrometry. Thus, 133.9 g (yield: 93.0%) of the object 2-methyl-2-adamantyl α-trifluoromethylacrylate was obtained.
Workup
- customA 500 ml flask was flushed with nitrogen
- customAfter completion of the reaction
- washthe neutralized liquid was washed with an aqueous saturated sodium chloride solution
Sources & evidence
- ORD record
- ord-5087dbe0678d4eaf81775c0dcbdce07c
- Source dataset
- uspto-grants-2006_12
- Patent number
- US07148363B2
Linked notes
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