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

HRID 512021
Notes
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Reaction equation

HRID 512021 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 123431,4-CyclohexadieneHCID 25018865N-[4-(4-Benzyloxy-phenoxy)-butyl]saccharin

Product 1

HCID 25018869N-[4-(4-Hydroxy-phenoxy)-butyl]saccharinYield 56%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

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

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe catalyst was removed by filtration through Celite
  3. customthe filtrate was evaporated under reduced pressure
  4. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes