1,4-Dimethoxybenzene → HCID 19753590, compound
Reaction equation
SCCCCCCCCC1C=C(O)C=CC=1O.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1.C([Li])CCC.[Br:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41]Br>>[Br:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][C:24]1[CH:25]=[C:20]([O:19][CH3:18])[CH:21]=[CH:22][C:23]=1[O:26][CH3:27]Participants
Procedure
Au microelectrodes (approximately 103 μm2) or Au macroelectrodes (approximately 1 cm2) can be modified with QH2 or Fc by dipping the Au into solutions containing one or both of the thiol reagents. Preparation of 2-(8-mercapto-octyl)hydroquinone involves several steps: 1,4-dimethoxy-benzene was deprotonated with n-butyllithium and added to excess 1,8-dibromo-octane; vacuum distillation afforded 2-(8-bromo-octyl)-1,4-dimethoxybenzene; demethylation was accomplished in quantitative yield with BBr3 ; the bromide was displaced by thioacetate; and subsequent hydrolysis under acidic conditions yields the thiol which was purified by chromatography. Materials were characterized by 1H NMR spectroscopy. Anal. Calcd (Found) for C14H22O2S: C, 66.10 (66.21); H, 8.72 (8.58); S, 12.60 (12.57). The molecules self-assemble onto the Au surfaces when the Au is placed into approximately 1 mM solution of Fc or QH2 in tetrahydrofuran (THF) or ethanol:hexane, 1:1. Mixtures of Fc and QH2 self-assemble onto Au from a QH2 :Fc, 2:1 mixture in THF or in ethanol:hexane, 1:1, at a total thiol concentration of approximately 1 mM. All derivatizations were carried out under argon at 25° C. for approximately 24 hr.
Workup
- additioncontaining one
- distillationvacuum distillation
Sources & evidence
- ORD record
- ord-519514be4bc74f93b615ceba09848a86
- Source dataset
- uspto-grants-1993_06
- Patent number
- US05223117
Reaction notes
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