Sodium 4-hydroxybenzenesulfonate synthesis
- Product Name:Sodium 4-hydroxybenzenesulfonate
- CAS Number:825-90-1
- Molecular formula:C6H7NaO4S
- Molecular Weight:198.17
98-67-9
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Yield:-
Reaction Conditions:
with sodium hydride in N,N-dimethyl-formamide at 0 - 20; for 0.5 h;Inert atmosphere;
Steps:
7.D Step D:
synthesis of sulfo-phenoxy dye
A solution of disodium salt of 4-hydroxybenzene sulfonic acid was prepared as follows: To a suspension of 60% sodium hydride (120 mg, 3 mmol of 100% NaH) in 10 ml of dry DMF, cooled to 0 °C under nitrogen was added a DMF solution (10 ml) of 4-hydroxy benzene sulfonic acid dihydrate, (2 mmol, ALDRICH).
After 10 min. the reaction contents were warmed to room temperature for 20 min.
Then, the contents were transferred to a flask containing 1 mmol of the chloro dye in 30 ml of DMF with vigorous stirring at room temperature.
The reaction was monitored by UV-Vis absorption spectrum that showed a hypsochromic shift from 782 nm to 769 nm.
After 30 min., the reaction was quenched with dry ice.
DMF was evaporated on a rotovap.
Precipitation with ether furnished the crude product as a dry powder that was further purified by reversed phase C18 silica by gel column using 40% aq. methanol.
Yield 75%.
The pure product was characterized by proton NMR.
References:
LI-COR, INC.;KOVAR, Joy;CHEN, Jiyan;DRANEY, Daniel R.;OLIVE, D. Michael;VOLCHECK, William M.;XU, Xinshe;LUGADE, Ananda G.;NARAYANAN, Narasimhachari EP2035505, 2016, B1 Location in patent:Paragraph 0184; 0188
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