2,6-di-tert-butyl-4-[2-(4-methoxy-benzyl)-1,1-dioxo-1λ⁶-isothiazolidin-5-ylidenemethyl]-phenol

Base Information

• Chemical Name: 2,6-di-tert-butyl-4-[2-(4-methoxy-benzyl)-1,1-dioxo-1λ⁶-isothiazolidin-5-ylidenemethyl]-phenol
• CAS No.: 279669-73-7
• Molecular Formula: C₂₆H₃₅NO₄S
• Molecular Weight: 457.634

Synonyms:2,6-di-tert-butyl-4-[2-(4-methoxy-benzyl)-1,1-dioxo-1λ⁶-isothiazolidin-5-ylidenemethyl]-phenol

Chemical Property of 2,6-di-tert-butyl-4-[2-(4-methoxy-benzyl)-1,1-dioxo-1λ⁶-isothiazolidin-5-ylidenemethyl]-phenol

Chemical Property:

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Technology Process of 2,6-di-tert-butyl-4-[2-(4-methoxy-benzyl)-1,1-dioxo-1λ⁶-isothiazolidin-5-ylidenemethyl]-phenol

There total 6 articles about 2,6-di-tert-butyl-4-[2-(4-methoxy-benzyl)-1,1-dioxo-1λ⁶-isothiazolidin-5-ylidenemethyl]-phenol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(3,5-di-tert-butyl-4-methoxymethoxy-phenyl)-[2-(4-methoxy-benzyl)-1,1-dioxo-1λ6-isothiazolidin-5-yl]-methanol (223579-40-6) → 2,6-di-tert-butyl-4-[2-(4-methoxy-benzyl)-1,1-dioxo-1λ6-isothiazolidin-5-ylidenemethyl]-phenol (279669-73-7)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; for 0.5h; Heating;

DOI:10.1021/jm9906015

Reference yield:

2-(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3-dioxolane (74222-81-4) → 2,6-di-tert-butyl-4-[2-(4-methoxy-benzyl)-1,1-dioxo-1λ6-isothiazolidin-5-ylidenemethyl]-phenol (279669-73-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: NaH / tetrahydrofuran; dimethylformamide / 0.17 h

1.2: 80 percent / tetrahydrofuran; dimethylformamide / 1 h

2.1: 100 percent / aq. HCl / acetone / 1 h

3.1: diisopropylamine; BuLi; hexamethylphosphamide / hexane; tetrahydrofuran / 0.5 h / -78 °C

4.1: p-TsOH / toluene / 0.5 h / Heating

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; sodium hydride; toluene-4-sulfonic acid; diisopropylamine; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; acetone; toluene; 1.1: Metallation / 1.2: Substitution / 2.1: Hydrolysis / 3.1: Addition / 4.1: Dehydration;

DOI:10.1021/jm9906015

Reference yield:

2-(4-methoxybenzyl)-1,2-isothiazolidine-1,1-dioxide (158089-76-0) → 2,6-di-tert-butyl-4-[2-(4-methoxy-benzyl)-1,1-dioxo-1λ6-isothiazolidin-5-ylidenemethyl]-phenol (279669-73-7)

Guidance literature:

Multi-step reaction with 2 steps

1: diisopropylamine; BuLi; hexamethylphosphamide / hexane; tetrahydrofuran / 0.5 h / -78 °C

2: p-TsOH / toluene / 0.5 h / Heating

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; toluene-4-sulfonic acid; diisopropylamine; In tetrahydrofuran; hexane; toluene; 1: Addition / 2: Dehydration;

DOI:10.1021/jm9906015

upstream raw materials:

(3,5-di-tert-butyl-4-methoxymethoxy-phenyl)-[2-(4-methoxy-benzyl)-1,1-dioxo-1λ⁶-isothiazolidin-5-yl]-methanol

2-(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3-dioxolane

2-(4-methoxybenzyl)-1,2-isothiazolidine-1,1-dioxide

4-Methoxymethoxy-3,5-di-tert-butylbenzaldehyde

Downstream raw materials:

(E)-5-(3,5-di-tert-butyl-4-hydroxybenzylidene)isothiazolidine 1,1-dioxide

{5-[1-(3,5-Di-tert-butyl-4-hydroxy-phenyl)-meth-(E)-ylidene]-1,1-dioxo-1λ⁶-isothiazolidin-2-yl}-acetic acid ethyl ester

(E)-5-(3,5-di-tert-butyl-4-hydroxybenzylidene)-2-(N-methoxymethyl-N-benzyloxycarbamoyl)-1,2-isothiazolidine-1,1-dioxide

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