Isopropanol → HCID 54516213, compound

HRID 1647000Notes

Reaction equation

HRID 1647000 reaction equation
[CH3:1][C:2]1[CH:7]([OH:8])[C:6]([CH3:10])(C)[CH:5]=[C:4]([C:11]([CH3:21])=[CH:12][C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([CH3:20])[CH:14]=2)[CH:3]=1.[CH2:22](C1OC1)Cl.C(O)(C)C.[OH-].[Na+]>O>[CH3:10][C:6]1[CH:5]=[C:4]([C:11]([CH3:21])=[CH:12][C:13]2[CH:14]=[C:15]([CH3:20])[C:16]([OH:19])=[C:17]([CH3:22])[CH:18]=2)[CH:3]=[C:2]([CH3:1])[C:7]=1[OH:8]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 7835Epichlorohydrin3×HCID 14798Sodium Hydroxide5×HCID 67882384HCID 67882384, compound

Product 1

HCID 54516213HCID 54516213, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
55 °C

Procedure

3,3',5,5-Tetramethyl-4,4'-dihydroxy-alphamethylstilbene (211.78 grams, 1.50 hydroxyl equivalent) from A. above, epichlorohydrin (693.98 grams, 7.50 moles), deionized water (60.35 grams, 8.0 percent by weight of the epichlorohydrin used) and isopropanol (373.68 grams, 35 percent by weight of the epichlorohydrin used) are added to a two liter glass resin kettle reactor equipped with a chilled water condenser, mechanical stirrer, nitrogen purge (1 liter per minute), thermometer and thermostatically controlled infrared heating lamps and heated to 55° C. with stirring under a nitrogen atmosphere. Once the 55° C. reaction temperature is achieved, sodium hydroxide (54.0 grams, 1.35 mole) dissolved in deionized water (216 grams) is added dropwise to the reactor over a 45 minute period, so as to maintain reaction temperature between 55 and 58° C. Ten minutes after completion of the aqueous sodium hydroxide addition, the stirring is stopped and the aqueous layer which separates from the reaction mixture is pipetted off and discarded. Stirring is resumed and after a total of twenty minutes following completion of the initial aqueous sodium hydroxide addition, a second solution of sodium hydroxide (24.0 grams, 0.60 mole) dissolved in deionized water (96 grams) is added to the reactor over a twenty minute period and so as to maintain the 55° C. reaction temperature. Fifteen minutes after completion of the aqueous sodium hydroxide addition, the recovered reaction mixture is added to a separatory funnel and washed with 500 milliliters of deionized water. The separated organic layer is washed a second time (500 milliliters deionized water), recovered and then rotary evaporated under vacuum for 45 minutes at 110° C. then 30 minutes at 140° C. and 5 mm Hg. The product is recovered (293.84 grams) as a light amber colored, transparent liquid (at 24° C.) with an epoxide equivalent weight of 227.80.

Workup

  1. additionare added to a two liter glass resin kettle reactor
  2. customequipped with a chilled water condenser, mechanical stirrer
  3. customnitrogen purge (1 liter per minute)
  4. temperaturethermometer and thermostatically controlled infrared heating lamps
  5. customOnce the 55° C. reaction temperature
  6. additionis added dropwise to the reactor over a 45 minute period
  7. temperatureso as to maintain
  8. customreaction temperature between 55 and 58° C
  9. stirringStirring
  10. customafter a total of twenty minutes
  11. additionis added to the reactor over a twenty minute period
  12. temperatureso as to maintain
  13. customthe 55° C. reaction temperature
  14. customthe recovered reaction mixture
  15. additionis added to a separatory funnel
  16. washwashed with 500 milliliters of deionized water
  17. washThe separated organic layer is washed a second time (500 milliliters deionized water)
  18. customrecovered
  19. customrotary evaporated under vacuum for 45 minutes at 110° C.
  20. custom30 minutes
  21. customat 140° C.
  22. customThe product is recovered (293.84 grams) as a light amber colored, transparent liquid (at 24° C.) with an epoxide equivalent weight of 227.80

Sources & evidence

ORD record
ord-f789a81c14304dbfacc95671b76f7d99
Source dataset
uspto-grants-1993_01
Patent number
US05182340

Reaction notes

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