Sodium Hydroxide → Diglycidyl ether

HRID 1492350Notes

Reaction equation

HRID 1492350 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]1

Participants

4

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

  1. customas used in Preparation 1)
  2. additionwere mixed
  3. temperaturecooled to room temperature
  4. extractionThe mixture was extracted trice with chloroform
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent
  8. 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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