Sodium Hydroxide → Diglycidyl ether
Reaction equation
[CH2:1]1[O:3][C@H:2]1[CH2:4]Cl.[OH-:6].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[CH2:4]([O:6][CH2:4][CH:2]1[O:3][CH2:1]1)[CH:2]1[O:3][CH2:1]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
2.01 g of R-(-)-epichlorohydrin and 16 mg of benzyl triethyl ammonium chloride (the latter two compounds were the same ones as used in Preparation 1) were mixed and heated to 70° C. To the mixture was dropwise added 650 mg of 24% by weight sodium hydroxide aqueous solution. The resultant was stirred for 2 hours at 70° C., and cooled to room temperature. The mixture was extracted trice with chloroform, dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent. The residue was recrystallized from hexane to obtain 380 mg of an S isomer of glycidyl ether of the following formula: ##STR42## mp: 65° C. [α]D25 : +1.90° (C=0.46, CH2Cl2)
Workup
- customas used in Preparation 1)
- additionwere mixed
- temperaturecooled to room temperature
- extractionThe mixture was extracted trice with chloroform
- dry with materialdried over anhydrous magnesium sulfate
- distillationdistilled under reduced pressure
- customto remove the solvent
- customThe residue was recrystallized from hexane
Sources & evidence
- ORD record
- ord-cbf60dfc2a5b4d91bb8bce1a8dee0df1
- Source dataset
- uspto-grants-1994_12
- Patent number
- US05374373
Reaction notes
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