Sodium hydride → Methyl 3-(2'-chloro-4'-trifluoromethylphenoxy)-benzoxyacetate
Reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:5]=1[O:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[CH2:10][OH:11].Br[CH2:24][C:25]([O:27][CH3:28])=[O:26]>O1CCCC1>[Cl:3][C:4]1[CH:18]=[C:17]([C:19]([F:21])([F:20])[F:22])[CH:16]=[CH:15][C:5]=1[O:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[CH2:10][O:11][CH2:24][C:25]([O:27][CH3:28])=[O:26]Participants
Conditions
- Temperature
- 40 °C
Procedure
3.25 parts by weight of 80% strength sodium hydride were suspended in 100 parts by volume of absolute tetrahydrofuran and a solution of 30 parts by weight of 3-(2'-chloro-4'-trifluoromethylphenoxy)-benzyl alcohol in 50 parts by volume of absolute tetrahydrofuran was then added, a little at a time. The mixture was stirred at 40° C. for half an hour and a solution of 15 parts by weight of methyl bromoacetate in 50 parts by volume of absolute tetrahydrofuran was added. The reaction mixture was then stirred at the boil for 2 hours, and was cooled and concentrated under reduced pressure. The oily residue was taken up in ether, and the organic phase was extracted with water, dried with magnesium sulfate and evaporated down under reduced pressure. Fractional distillation of the residue gave 19 parts by weight (51% of theory) of methyl 3-(2'-chloro-4'-trifluoromethylphenoxy)-benzoxyacetate (compound No. 4) of boiling point 150°-160° C./0.2 bar and refractive index nD25 : 1.5268.
Workup
- stirringThe reaction mixture was then stirred at the boil for 2 hours
- temperaturewas cooled
- concentrationconcentrated under reduced pressure
- extractionthe organic phase was extracted with water
- dry with materialdried with magnesium sulfate
- customevaporated down under reduced pressure
- distillationFractional distillation of the residue
Sources & evidence
- ORD record
- ord-d7a7de992036447ca7428ab82af59cff
- Source dataset
- uspto-grants-1988_05
- Patent number
- US04744812
Reaction notes
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