Epichlorohydrin → HCID 9833572, compound

HRID 1582859Notes

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-].[Na+].[CH2:80]([CH:82]1[O:84][CH2:83]1)[Cl:81]>O>[CH2:80]([CH:82]1[O:84][CH2:83]1)[Cl:81].[CH2:67]([OH:68])[C@H:37]1[O:38][C@@H:39]2[O:44][C@H:45]3[C@H:50]([OH:51])[C@@H:49]([OH:52])[C@@H:48]([O:53][C@H:54]4[C@H:60]([OH:61])[C@@H:59]([OH:62])[C@@H:57]([O:58][C@H:3]5[C@H:4]([OH:76])[C@@H:5]([OH:75])[C@@H:6]([O:8][C@H:9]6[C@H:14]([OH:15])[C@@H:13]([OH:16])[C@@H:12]([O:17][C@H:18]7[C@H:23]([OH:24])[C@@H:22]([OH:25])[C@@H:21]([O:26][C@H:27]8[C@H:32]([OH:33])[C@@H:31]([OH:34])[C@@H:30]([O:35][C@H:36]1[C@H:41]([OH:42])[C@H:40]2[OH:43])[O:29][C@@H:28]8[CH2:69][OH:70])[O:20][C@@H:19]7[CH2:71][OH:72])[O:11][C@@H:10]6[CH2:73][OH:74])[O:7][C@@H:2]5[CH2:1][OH:77])[O:56][C@@H:55]4[CH2:63][OH:64])[O:47][C@@H:46]3[CH2:65][OH:66]

Participants

Conditions

Temperature: 30 °C

Procedure

β-Cyclodextrin (0.5 gm, 0.38 mmol) and sodium hydroxide (0.18 gm, 4.5 mmol) were dissolved in water (0.8 mL) and heated to 30° C. To this solution was added epichlorohydrin (0.345 mL, 4.4 mmol) and the immiscible solutions were stirred at 30° C. for 3.5 h, during which time the epichlorohydrin dissolved in the aqueous solution. The epichlorohydrin-β-cyclodextrin copolymer was then precipitated by the addition of acetone (10 mL). The acetone was decanted and the precipitate was dissolved in water (20 mL) and dialyzed in 14,000 molecular weight cutoff tubing against 2×1L water for 48 h. The polymer was then isolated by lyophilization to yield 0.3 gm of polymer.

Workup

dissolutiondissolved in the aqueous solution
customThe epichlorohydrin-β-cyclodextrin copolymer was then precipitated by the addition of acetone (10 mL)
customThe acetone was decanted
dissolutionthe precipitate was dissolved in water (20 mL)
customdialyzed in 14,000 molecular weight cutoff
customThe polymer was then isolated by lyophilization

Sources & evidence

ORD record: ord-1cb0531603614c27b815ecf0efb80589
Source dataset: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06740643B2

Reaction notes

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