p-Toluenesulfonic acid → HCID 14618490, compound

HRID 1165297Notes

Reaction equation

[C:1]1([OH:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH:12]1[C:24]2[C:23](=O)[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]=2[CH:15]=[CH:14][CH:13]=1.ClC(Cl)(Cl)C.[C:31]1([CH3:41])[CH:36]=[CH:35][C:34](S(O)(=O)=O)=[CH:33][CH:32]=1.S[CH2:43][CH2:44][C:45]([OH:47])=O>C(O)(C)C>[OH:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:23]1([C:44]2[CH:43]=[CH:41][C:31]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:45]=2[OH:47])[C:22]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:16]2[C:24]1=[CH:12][CH:13]=[CH:14][CH:15]=2

Participants

Conditions

Temperature: 90 °C

Procedure

BNFL was synthesized by charging 1-naphthol, 9-fluorenone, 1,1,1-trichloroethane, p-toluenesulfonic acid, and 3-mercaptopropionic acid to a stirred reactor in a molar ratio of 8:1:4:0.5:0.1 and heated to 90° C. for 2 hours under nitrogen and a reflux condenser. After 5 minutes at 90° C. crystals formed in the reaction mass. When the reaction mass went solid with crystals, more 1,1,1-trichloroethane was added and the reaction was continued. The reaction mass was cooled by the addition of a portion of isopropyl alcohol (IPA) and the product removed by filtration and washed with IPA. BNFL was obtained in 91% yield as white crystals with melting point=268°-290° C. The chemical structure for BNFL was supported by C13 and Proton solution NMR.

Workup

customBNFL was synthesized
customAfter 5 minutes at 90° C. crystals formed in the reaction mass
additionwas added
customthe product removed by filtration
washwashed with IPA
customBNFL was obtained in 91% yield as white crystals with melting point=268°-290° C

Sources & evidence

ORD record: ord-2a29f1c514fc4385b064cf0da3e771c9
Source dataset: uspto-grants-1990_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04908424

Reaction notes

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