1,4-Cyclohexadiene → N-[4-(4-Hydroxy-phenoxy)-butyl]saccharin

HRID 512021Notes

Reaction equation

C([O:8][C:9]1[CH:31]=[CH:30][C:12]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][N:18]2[C:28](=[O:29])[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[S:19]2(=[O:21])=[O:20])=[CH:11][CH:10]=1)C1C=CC=CC=1.C1CC=CCC=1>CCO.[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][N:18]2[C:28](=[O:29])[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[S:19]2(=[O:21])=[O:20])=[CH:30][CH:31]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of 83.3 (0.1 g, 0.23 mmol) in EtOH (5 mL) was added 10% Pd/C (0.1 g, 100% w/w) and 1,4-cyclohexadiene (92 mg, 1.15 mmol) and the resulting suspension was stirred vigorously at 50° C. for 2 hours. The reaction mixture was cooled to room temperature, the catalyst was removed by filtration through Celite, and the filtrate was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel (60% diethyl ether-hexane) to give 84 (0.044 g, 56% yield) as a white solid (m p 107-109° C.). 1H NMR (500 MHz, CDCl3) δ 8.06 (d, J=7.0 Hz, 1H), 7.92 (d, J=7.0 Hz, 1H), 7.87 (td, J=7.0 Hz, J=1.2 Hz, 1H), 7.83 (td, J=7.0 Hz, J=1.2 Hz, 1H), 6.79 (d, J=9.0 Hz, 2H), 6.74 (d, J=9.0 Hz, 2H), 4.38 (br s, 1H), 3.96 (t, J=6.4 Hz, 2H), 3.89 (t, J=7.2 Hz, 2H), 2.05 (quintet, J=6.9 Hz, 2H), 1.89 (quintet, J=6.9 Hz, 2H).

Workup

temperatureThe reaction mixture was cooled to room temperature
customthe catalyst was removed by filtration through Celite
customthe filtrate was evaporated under reduced pressure
customThe residue was purified by flash column chromatography on silica gel (60% diethyl ether-hexane)

Sources & evidence

ORD record: ord-43f34ebeeaec4617aa2e41ce8037bcf8
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102622B2

Reaction notes

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