Reaction equation
C(OC1C=CC(C(C2C=CC(OC(=O)C=C)=CC=2)(C2C=CC(OC(=O)C=C)=CC=2)C)=CC=1)(=O)C=C.[C:36]1([C:42]2[CH:51]=[CH:50][CH:49]=[C:48]([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)[C:43]=2[O:44][CH:45](O)[CH3:46])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.[C:58]([OH:62])(=[O:61])[CH:59]=[CH2:60].CS(O)(=O)=O>C1(C)C=CC=CC=1>[C:58]([O:62][CH2:46][CH2:45][O:44][C:43]1[C:48]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)=[CH:49][CH:50]=[CH:51][C:42]=1[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)(=[O:61])[CH:59]=[CH2:60]Participants
6
Procedure
To a 50 ml 1 neck round bottom equipped with a dean stark trap was added 2,6-diphenylphenoxyethanol (5 g, 1 eq), toluene (21 ml), acrylic acid (2.7 g, 2.2 eq), methane sulfonic acid (0.3 g, 0.18 eq), Prostab 5198 (0.003 g) and heated to reflux. After 3 hours the reaction was complete. The reaction was washed with 20 ml sodium carbonate and 20 ml sodium chloride brine. The toluene mixture was filtered through thin layer of silica gel and eluted with 30 ml toluene. The filtrate was treated with the “Prostab 5198” (0.003 g) and concentrated invacuo to recover a viscous oil. >97% by GC. RI=1.6062 at 25° C.
Workup
- temperatureheated to reflux
- washThe reaction was washed with 20 ml sodium carbonate and 20 ml sodium chloride brine
- filtrationThe toluene mixture was filtered through thin layer of silica gel
- washeluted with 30 ml toluene
- additionThe filtrate was treated with the “Prostab 5198” (0.003 g)
- concentrationconcentrated invacuo
- customto recover a viscous oil
- customat 25° C.
Sources & evidence
- ORD record
- ord-ac5f5e343a9943e7a4e8baf1a5a5c939
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08871315B2
Linked notes
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