N-Hydroxyphthalimide → N-(3-trifluoromethylbenzyloxy)phthalimide
Reaction equation
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].C([O-])(=O)C.[Na+].[F:18][C:19]([F:29])([F:28])[C:20]1[CH:21]=[C:22]([CH2:26]Cl)[CH:23]=[CH:24][CH:25]=1>CS(C)=O>[F:18][C:19]([F:28])([F:29])[C:20]1[CH:21]=[C:22]([CH2:26][O:1][N:2]2[C:3](=[O:12])[C:4]3=[CH:11][CH:10]=[CH:9][CH:8]=[C:5]3[C:6]2=[O:7])[CH:23]=[CH:24][CH:25]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A solution of 8.0 grams (0.049 mole) of N-hydroxyphthalimide and 4.0 grams (0.059 mole) of sodium acetate in about 25 mL of dimethyl sulfoxide was stirred, and a solution of 11.5 grams (0.059 mole) of 3-trifluoromethylphenylmethyl chloride in about 15 mL of dimethyl sulfoxide was added dropwise during a 10 minute period. Upon completion of addition, the reaction mixture was heated to about 60° C. where it stirred until there was no apparent color change in the reaction mixture. The reaction mixture was then poured into an ice-water mixture. The resultant solid was collected and washed with water. The solid was then recrystallized with 100 mL of ethanol. The solid was collected by filtration and dried, yielding 12.2 grams of N-(3-trifluoromethylphenylmethoxy)phthalimide, mp 106°-108° C. The NMR spectrum was consistent with the proposed structure.
Workup
- additionUpon completion of addition
- customThe resultant solid was collected
- washwashed with water
- customThe solid was then recrystallized with 100 mL of ethanol
- filtrationThe solid was collected by filtration
- customdried
Sources & evidence
- ORD record
- ord-49885d26a30a45aea5b1706d7eeb5f1f
- Source dataset
- uspto-grants-1998_01
- Patent number
- US05712281
Reaction notes
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