SODIUM OCTYL SULFATE synthesis

Yield:-

Reaction Conditions:

with sodium hydrogensulfite in ethanol;water;ethyl acetate for 4 h;Cooling with ice;Inert atmosphere;

Steps:

General Procedure for the Reduction of Weinreb Amides to Aldehydes.
General procedure: The following procedure for the reduction of N-methoxy-N-methylbenzamide by MgAB is representative. To an oven-dried and argon cooled 25-mL round-bottom flask equippedwith a stir bar and septa was added N-methoxy-N-methylbenzamide (0.305 mL, 2 mmol)followed by THF (1.7 mL). Chloromagnesium dimethylaminoborohydride (MgAB, 2mL, 1M, 2 mmol) was then added dropwise via a syringe. The reaction was monitored byTLC (Hex/EtOAc, 1:1). After 30 min, the reaction solution was added dropwise to a solution of acetaldehyde (2 mmol) and acetic acid (2 mmol) in pentane (10 mL). After 15min, saturated aqueous NH4Cl (2 mL) was added. The organic layer was separated and the aqueous phase was extracted with Et2O (2 x 10 mL). The combined organic layerswas washed with 1M HCl (10 mL), dried with magnesium sulfate, and concentratedunder reduced pressure to yield crude aldehyde as an orange oil. The crude aldehyde (2mmol) was transferred to a round-bottom flask equipped with a magnetic stir barfollowed by EtOH (3 mL) and EtOAc (5 mL) and cooled with an ice bath. A saturated aqueous solution of NaHSO3 (1 mL) was added with stirring. After 4 h, the solid bisulfite adduct was isolated by vacuum filtration, washed with Et2O (3 × 5 mL) and dried undervacuum to yield a white solid. The bisulfite adduct was then added to a round-bottom flask dissolved in H2O (10 mL) and a 37% formalin solution (2 mL) was added followedby Et2O (20 mL). The biphasic solution was stirred for 1 h. The aqueous layer was separated and extracted with a 1:1 mixture of THF/Et2O (3 x 10 mL). The combined organic layers was dried over magnesium sulfate, and concentrated under reduced pressure to give the aldehyde as a pale yellow oil (0.160 g, 1.5 mmol 75% yield).

References:

Bailey, Christopher L.;Clary, Jacob W.;Tansakul, Chittreeya;Klabunde, Lucas;Anderson, Christopher L.;Joh, Alexander Y.;Lill, Alexander T.;Peer, Natalie;Braslau, Rebecca;Singaram, Bakthan [Tetrahedron Letters,2015,vol. 56,# 5,p. 706 - 709] Location in patent:supporting information

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