Propylene Oxide → 2-Hydroxypropyl-Beta-Cyclodextrin

HRID 2371918Notes

Reaction equation

HRID 2371918 reaction equation
[CH2:1]([OH:77])[C@H:2]1[O:7][C@@H:6]2[O:8][C@H:9]3[C@H:14]([OH:15])[C@@H:13]([OH:16])[C@@H:12]([O:17][C@H:18]4[C@H:23]([OH:24])[C@@H:22]([OH:25])[C@@H:21]([O:26][C@H:27]5[C@H:32]([OH:33])[C@@H:31]([OH:34])[C@@H:30]([O:35][C@H:36]6[C@H:41]([OH:42])[C@@H:40]([OH:43])[C@@H:39]([O:44][C@H:45]7[C@H:50]([OH:51])[C@@H:49]([OH:52])[C@@H:48]([O:53][C@H:54]8[C@H:60]([OH:61])[C@@H:59]([OH:62])[C@@H:57]([O:58][C@H:3]1[C@H:4]([OH:76])[C@H:5]2[OH:75])[O:56][C@@H:55]8[CH2:63][OH:64])[O:47][C@@H:46]7[CH2:65][OH:66])[O:38][C@@H:37]6[CH2:67][OH:68])[O:29][C@@H:28]5[CH2:69][OH:70])[O:20][C@@H:19]4[CH2:71][OH:72])[O:11][C@@H:10]3[CH2:73][OH:74].[OH-:78].[Na+].[CH2:80]1[O:83][CH:81]1[CH3:82]>>[CH3:1][CH:2]([OH:7])[CH2:3][O:70][CH2:69][C@H:28]1[O:29][C@@H:30]2[O:35][C@H:36]3[C@H:41]([OH:42])[C@@H:40]([OH:43])[C@@H:39]([O:44][C@H:45]4[C@H:50]([OH:51])[C@@H:49]([OH:52])[C@@H:48]([O:53][C@H:54]5[C@H:60]([OH:61])[C@@H:59]([OH:62])[C@@H:57]([O:58][C@H:3]6[C@H:4]([OH:76])[C@@H:5]([OH:75])[C@@H:6]([O:8][C@H:9]7[C@H:14]([OH:15])[C@@H:13]([OH:16])[C@@H:12]([O:17][C@H:18]8[C@H:23]([OH:24])[C@@H:22]([OH:25])[C@@H:21]([O:26][C@H:27]1[C@H:32]([OH:33])[C@H:31]2[OH:34])[O:20][C@@H:19]8[CH2:71][O:72][CH2:4][CH:5]([OH:78])[CH3:6])[O:11][C@@H:10]7[CH2:73][O:74][CH2:14][CH:9]([OH:8])[CH3:10])[O:7][C@@H:2]6[CH2:1][O:77][CH2:28][CH:27]([OH:26])[CH3:32])[O:56][C@@H:55]5[CH2:63][O:64][CH2:37][CH:36]([OH:35])[CH3:41])[O:47][C@@H:46]4[CH2:65][O:66][CH2:19][CH:18]([OH:17])[CH3:23])[O:38][C@@H:37]3[CH2:67][O:68][CH2:80][CH:81]([OH:83])[CH3:82]

Participants

4

Reactant 3

HCID 6378Propylene OxideHCID 14798Sodium HydroxideHCID 444041beta-Cyclodextrin

Product 1

HCID 140496892-Hydroxypropyl-Beta-Cyclodextrin

Procedure

β-Cyclodextrin (500 g hydrate, i.e., 432 g anhydous, 0.382 mole) was as above dissolved in a solution of sodium hydroxide (45 g, 1.1 mole in 750 mL distilled water, i.e., 5.7% W/W) and under the same conditions as above treated with propylene oxide (260 mL, 217 g, 3.73 mole). The reaction mixture was left for five hours in an ice bath and kept at room temperature for two days. After processing similar to that described above and including extraction of oligopropylene glycols with acetone a white powder of hydroxypropyl-β-cyclodextrin (490 g) was obtained.

Workup

  1. waitkept at room temperature for two days
  2. extractionextraction of oligopropylene glycols with acetone a white powder of hydroxypropyl-β-cyclodextrin (490 g)
  3. customwas obtained

Sources & evidence

ORD record
ord-35642a9470f24f3a92ec2c03df4b7380
Source dataset
uspto-grants-1992_03
Patent number
US05096893

Reaction notes

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