Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 69492200, compound

HRID 855466Notes

Reaction equation

O1CCCCC1[O:7][C@H:8]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[CH2:9][O:10][C:11](=[O:41])[CH:12]=[CH:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21](=[O:40])[C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][O:35][C:36](=[O:39])[CH:37]=[CH2:38])=[CH:24][CH:23]=2)=[CH:16][CH:15]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(O)C.COC1C=CC(O)=CC=1>[OH:7][C@H:8]([C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)[CH2:9][O:10][C:11](=[O:41])[CH:12]=[CH:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21](=[O:40])[C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][O:35][C:36](=[O:39])[CH:37]=[CH2:38])=[CH:24][CH:23]=2)=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 55 °C

Procedure

6.4 g of (R)-4-(4-(6-Acryloyloxyhexyloxy)benzoyloxy)cinnamic acid 2-(tetrahydropyran-2-yloxy)-2-phenyl-ethyl ester (20) (9.8 mmole) were dissolved in 35 ml of absolute ethanol and 0.5 g (2 mmole) of pyridinium 4-toluensulfonate and 40 mg of 4-methoxyphenol (to avoid polymerization) were added. The mixture was heated at 55° C. for 20 h. After cooling to room temperature, a white powder precipitated. It was filtered and washed with ethanol. It was dried in a dessicator with silica. 3 g of a white solid (55%) were obtained.

Workup

temperatureAfter cooling to room temperature
customa white powder precipitated
filtrationIt was filtered
washwashed with ethanol
customIt was dried in a dessicator with silica

Sources & evidence

ORD record: ord-22badef9671149f4aa4ad6be73778b77
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07261836B2

Reaction notes

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