反応 #42056

反応方程式

sodium bromate

sodium hydrogensulfite

4-methyl-3-trifluoromethylbenzoic acid

isopropyl acetate

→

objective compound

収率 60.1%

4-(bromomethyl)-3-trifluoromethylbenzoic acid

収率 60.1%

溶媒

water

water

反応条件

後処理

1. 1
   温度The mixture was gradually heated from 30° C. up to 50° C. at intervals of 10° C.
2. 2
   workup.STIRRINGstirred until the color of the reaction solution
3. 3
   その他The aqueous layer was separated
4. 4
   その他to remove
5. 5
   workup.ADDITIONto the organic layer were added a solution of 133.0 g of sodium bromate in 420 ml of water
6. 6
   温度a solution of 91.7 g of sodium hydrogensulfite in 180 ml of water, and then the mixture was gradually heated up to 60° C. as above
7. 7
   その他After separation
8. 8
   workup.ADDITIONto the organic layer were further added a solution of 133.0 g of sodium bromate in 420 ml of water
9. 9
   温度a solution of 91.7 g of sodium hydrogensulfite in 180 ml of water, and the mixture was gradually heated as above and
10. 10
    温度heated to the temperature the mixture
11. 11
    温度was finally refluxed
12. 12
    その他After the completion of the reaction
13. 13
    その他the reaction solution was separated
14. 14
    洗浄the organic layer was washed twice with a 5% aqueous sodium thiosulfate solution and twice with 15% saline
15. 15
    乾燥dried over anhydrous magnesium sulfate
16. 16
    workup.DISTILLATIONthe solvent was distilled off under reduced pressure
17. 17
    workup.ADDITIONTo the residue was added 120 ml of n-heptane
18. 18
    workup.STIRRINGthe mixture was stirred
19. 19
    ろ過the crystals were collected by filtration

実験手順

To 60.0 g of 4-methyl-3-trifluoromethylbenzoic acid was added 600 ml of isopropyl acetate. Under stirring at room temperature, a solution of 133.0 g of sodium bromate in 420 ml of water and a solution of 91.7 g of sodium hydrogensulfite in 180 ml of water were added in turn. The mixture was gradually heated from 30° C. up to 50° C. at intervals of 10° C. and stirred until the color of the reaction solution disappeared. The aqueous layer was separated to remove, and to the organic layer were added a solution of 133.0 g of sodium bromate in 420 ml of water and a solution of 91.7 g of sodium hydrogensulfite in 180 ml of water, and then the mixture was gradually heated up to 60° C. as above. After separation, to the organic layer were further added a solution of 133.0 g of sodium bromate in 420 ml of water and a solution of 91.7 g of sodium hydrogensulfite in 180 ml of water, and the mixture was gradually heated as above and heated to the temperature the mixture was finally refluxed. After the completion of the reaction, the reaction solution was separated, the organic layer was washed twice with a 5% aqueous sodium thiosulfate solution and twice with 15% saline, dried over anhydrous magnesium sulfate, and, then the solvent was distilled off under reduced pressure. To the residue was added 120 ml of n-heptane, the mixture was stirred, and then the crystals were collected by filtration to obtain 50.0 g of the objective compound as colorless crystals.

出典