Isopropanol → 4,4-Dihydroxy-alpha-methylstilbene

HRID 326894

반응식

HRID 326894 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:17])=[CH:9][C:10]2[CH:15]=[CH:14][C:13](O)=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.C(C1[O:22]C1)Cl.C(O)(C)C.[OH-].[Na+]>O>[OH:1][C:2]1([OH:22])[CH:7]=[CH:6][C:5]([C:8]([CH3:17])=[CH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][CH2:3]1

참가 물질

6

반응물 4

HCID 3776IsopropanolHCID 7835Epichlorohydrin2회HCID 14798Sodium Hydroxide4회HCID 6566934,4'-Dihydroxy-alpha-methylstilbene

생성물 1

HCID 699336044,4-Dihydroxy-alpha-methylstilbene

시약·촉매·용매 1

HCID 962Water용매3회

반응 조건

온도
55 °C

실험 절차

4,4'-Dihydroxy-alpha-methylstilbene 152.73 grams, 1.35 hydroxyl equivalents) from A above, epichlorohydrin (624.58 grams, 6.75 moles), deionized water (54.31 grams, 8.0 percent by weight of the epichlorohyrin used) and isopropanol (336.31 grams, 35 percent by weight of the epichlorohydrin used) is added to a reactor and heated to 55° C. with stirring under a nitrogen atmosphere. Once the 55° C. reaction temperature is achieved, sodium hydroxide (48.6 grams, 1.22 moles) dissolves in deionized water (194.4 grams) is added dropwise to the reactor over a 45 minute period so as to maintain reaction temperature between 55° and 59° C. Ten minutes after completion of the aqueous sodium hydroxide addition, the stirring is stopped and the aqueous layer which separated 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 (21.6 grams, 0.54 mole) dissolved in deionized water (86.4 grams) is added to the reactor over a twenty minute period 30 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 750 milliliters of deionized water. The separated organic layer is washed a second time (750 milliliters deionized water), recovered and then rotary evaporated under vacuum for 45 minutes at 110° C. then 30 minutes at 130° C. The product is recovered (218.6 grams) as a crystalline solid with an epoxide equivalent weight of 183.33.

후처리

  1. additionis added to a reactor
  2. customOnce the 55° C. reaction temperature
  3. additionis added dropwise to the reactor over a 45 minute period so as
  4. temperatureto maintain
  5. customreaction temperature between 55° and 59° C
  6. customthe aqueous layer which separated from the reaction mixture
  7. stirringStirring
  8. customafter a total of twenty minutes
  9. additioncompletion of the initial aqueous sodium hydroxide addition
  10. additionis added to the reactor over a twenty minute period 30 as
  11. temperatureto maintain
  12. customthe 55° C. reaction temperature
  13. customthe recovered reaction mixture
  14. additionis added to a separatory funnel
  15. washwashed with 750 milliliters of deionized water
  16. washThe separated organic layer is washed a second time (750 milliliters deionized water)
  17. customrecovered
  18. customrotary evaporated under vacuum for 45 minutes at 110° C.
  19. custom30 minutes
  20. customat 130° C
  21. customThe product is recovered (218.6 grams) as a crystalline solid with an epoxide equivalent weight of 183.33

출처 및 근거

ORD 기록
ord-9824c80c642b4f3da2f21b708132930f
출처 데이터셋
uspto-grants-1993_12
특허 번호
US05270405

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