Piperonyl Butoxide → beta-Cyclodextrin piperonyl butoxide

HRID 1248399Notes

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].[CH3:78][CH2:79][CH2:80][CH2:81][O:82][CH2:83][CH2:84][O:85][CH2:86][CH2:87][O:88][CH2:89][C:90]1[CH:91]=[C:92]2[O:101][CH2:100][O:99][C:93]2=[CH:94][C:95]=1[CH2:96][CH2:97][CH3:98]>>[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].[CH3:78][CH2:79][CH2:80][CH2:81][O:82][CH2:83][CH2:84][O:85][CH2:86][CH2:87][O:88][CH2:89][C:90]1[CH:91]=[C:92]2[O:101][CH2:100][O:99][C:93]2=[CH:94][C:95]=1[CH2:96][CH2:97][CH3:98]

Participants

Reactant 2

HCID 5794Piperonyl Butoxide

HCID 444041beta-Cyclodextrin

Product 1

HCID 131714245beta-Cyclodextrin piperonyl butoxideYield 109.2%

Procedure

20 g (17.62 millimoles) of β-cyclodextrin and 5 ml (5.3 g, 15.6 millimoles) of piperonyl butoxide are homogenized in a pug mill under intensive kneading, whereupon the mixture is dried in a vacuum exsiccator over phosphorous pentoxide. Thus 25.1 g of an β-cyclodextrin-piperonyl butoxide inclusion complex are obtained. The product is a white crystalline not moist substance which is a little oily to the touch. The piperonyl butoxide content of the complex amounts to 20% which corresponds to a molar ratio of 0.84 mole of PBO/1 mole of β-cyclodextrin. The solubility of the complex amounts to 0.165 mg/ml, at 20° C., measured by shaking for an hour.

Workup

dry with materialis dried in a vacuum exsiccator over phosphorous pentoxide

Sources & evidence

ORD record: ord-f3d4225cb25a4ac39901cfc059a0dec8
Source dataset: uspto-grants-1985_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04524068

Reaction notes

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