3-tert-butyl-5-[1,1-dimethyl-2-(tetrahydropyran-2-yloxy)ethyl]-4-hydroxybenzaldehyde

Base Information

• Chemical Name: 3-tert-butyl-5-[1,1-dimethyl-2-(tetrahydropyran-2-yloxy)ethyl]-4-hydroxybenzaldehyde
• CAS No.: 499774-43-5
• Molecular Formula: C₂₀H₃₀O₄
• Molecular Weight: 334.456

Synonyms:3-tert-butyl-5-[1,1-dimethyl-2-(tetrahydropyran-2-yloxy)ethyl]-4-hydroxybenzaldehyde

Chemical Property of 3-tert-butyl-5-[1,1-dimethyl-2-(tetrahydropyran-2-yloxy)ethyl]-4-hydroxybenzaldehyde

Chemical Property:

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Technology Process of 3-tert-butyl-5-[1,1-dimethyl-2-(tetrahydropyran-2-yloxy)ethyl]-4-hydroxybenzaldehyde

There total 5 articles about 3-tert-butyl-5-[1,1-dimethyl-2-(tetrahydropyran-2-yloxy)ethyl]-4-hydroxybenzaldehyde 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: 97.0%

3,4-dihydro-2H-pyran (110-87-2) + 3-tert-butyl-4-hydroxy-5-(2-hydroxy-1,1-dimethylethyl)-benzaldehyde (112700-10-4) → 3-tert-butyl-5-[1,1-dimethyl-2-(tetrahydropyran-2-yloxy)ethyl]-4-hydroxybenzaldehyde (499774-43-5)

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane; at 20 ℃; for 0.666667h;

DOI:10.1021/jo020587v

Reference yield:

7-tert-butyl-3,3,5-trimethyl-3H-benzofuran-2-one (499774-39-9) → 3-tert-butyl-5-[1,1-dimethyl-2-(tetrahydropyran-2-yloxy)ethyl]-4-hydroxybenzaldehyde (499774-43-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / NaBH₄; MeOH / 1,2-dimethoxy-ethane / 23 - 75 °C

2: 72 percent / DMSO; HBr / H₂O / 1 h / 100 °C

3: 97 percent / PPTS / CH₂Cl₂ / 0.67 h / 20 °C

With methanol; sodium tetrahydroborate; hydrogen bromide; pyridinium p-toluenesulfonate; dimethyl sulfoxide; In 1,2-dimethoxyethane; dichloromethane; water;

DOI:10.1021/jo020587v

Reference yield:

6-tert-butyl-2-(2'-hydroxy-1',1'-dimethylethyl)-4-methylphenol (112700-14-8) → 3-tert-butyl-5-[1,1-dimethyl-2-(tetrahydropyran-2-yloxy)ethyl]-4-hydroxybenzaldehyde (499774-43-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / DMSO; HBr / H₂O / 1 h / 100 °C

2: 97 percent / PPTS / CH₂Cl₂ / 0.67 h / 20 °C

With hydrogen bromide; pyridinium p-toluenesulfonate; dimethyl sulfoxide; In dichloromethane; water;

DOI:10.1021/jo020587v

upstream raw materials:

3,4-dihydro-2H-pyran

3-tert-butyl-4-hydroxy-5-(2-hydroxy-1,1-dimethylethyl)-benzaldehyde

6-tert-butyl-2-(2'-hydroxy-1',1'-dimethylethyl)-4-methylphenol

7-tert-butyl-3,3-dimethyl-2-oxo-3H-benzofuran-5-carbaldehyde

Downstream raw materials:

2-tert-butyl-6-[1,1-dimethyl-2-(tetrahydro-pyran-2-yloxy)-ethyl]-4-[(2-ethyl-1,1-dioxo-1λ⁶-isothiazolidin-5-yl)-hydroxy-methyl]-phenol

(E)-5-[3-tert-butyl-4-hydroxy-5-(2-hydroxy-1,1-dimethyl-ethyl)]-benzylidene-2-ethyl-1,2-isothiazolidine-1,1-dioxide

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