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Isopropanol → 4,4-Dihydroxy-alpha-methylstilbene

HRID 326894
ノート
印刷プレビュー

反応式

HRID 326894 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 3776IsopropanolHCID 7835Epichlorohydrin2 回HCID 14798Sodium Hydroxide4 回HCID 6566934,4'-Dihydroxy-alpha-methylstilbene

生成物 1

HCID 699336044,4-Dihydroxy-alpha-methylstilbene

試薬・触媒・溶媒 1

HCID 962Water溶媒3 回

反応条件

温度
55 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9824c80c642b4f3da2f21b708132930f
出典データセット
uspto-grants-1993_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05270405

反応ノート

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