(S)-4-(2',5'-dimethoxyphenyl)-3-hydroxy-3-methylbutanal

Base Information

• Chemical Name: (S)-4-(2',5'-dimethoxyphenyl)-3-hydroxy-3-methylbutanal
• CAS No.: 300661-16-9
• Molecular Formula: C₁₃H₁₈O₄
• Molecular Weight: 238.284
• Mol file: 300661-16-9.mol

Synonyms:(S)-4-(2',5'-dimethoxyphenyl)-3-hydroxy-3-methylbutanal

Chemical Property of (S)-4-(2',5'-dimethoxyphenyl)-3-hydroxy-3-methylbutanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-(2',5'-dimethoxyphenyl)-3-hydroxy-3-methylbutanal

There total 11 articles about (S)-4-(2',5'-dimethoxyphenyl)-3-hydroxy-3-methylbutanal 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: 90.0%

(S)-4-(2',5'-dimethoxyphenyl)-3-methylbutane-1,3-diol (300661-19-2) → (S)-4-(2',5'-dimethoxyphenyl)-3-hydroxy-3-methylbutanal (300661-16-9)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; water; at 20 ℃; for 6h;

DOI:10.1071/CH99091

Reference yield:

(R)-(-)-citramalic acid (6236-10-8,2306-22-1) → (S)-4-(2',5'-dimethoxyphenyl)-3-hydroxy-3-methylbutanal (300661-16-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 10.02 g / CH₂Cl₂; ethanol / 0.5 h

2.1: 84 percent / LiAlH₄ / tetrahydrofuran / 18 h / Heating

3.1: 82 percent / p-toluenesulfonic acid / 24 h / 20 °C

4.1: NaH / tetrahydrofuran

4.2: 91 percent / tetrabutylammonium iodide / tetrahydrofuran / 24 h

5.1: 92 percent / aq. H₂SO₄ / tetrahydrofuran / 4 h / 40 °C

6.1: 91 percent / Et₃N / CH₂Cl₂ / 0.17 h / -10 °C

7.1: 94 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 1 h / 20 °C

8.1: Mg; I₂ / tetrahydrofuran / 4 h / Heating

8.2: 92 percent / dilithium tetrachlorocuprate / tetrahydrofuran / -78 - -20 °C

9.1: 97 percent / H₂ / 10 percent Pd/C / methanol / 12 h

10.1: 90 percent / 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one / CH₂Cl₂; H₂O / 6 h / 20 °C

With lithium aluminium tetrahydride; sulfuric acid; hydrogen; iodine; sodium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; magnesium; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; 1.1: Esterification / 2.1: Reduction / 3.1: cyclocondensation / 4.1: deprotonation / 4.2: benzylation / 5.1: Hydrolysis / 6.1: Esterification / 7.1: cyclocondensation / 8.1: Metallation / 8.2: Ring cleavage / 9.1: Hydrogenolysis / 10.1: Oxidation;

DOI:10.1071/CH99091

Reference yield:

(R)-dimethyl 2-hydroxy-2-methylsuccinate (81426-68-8) → (S)-4-(2',5'-dimethoxyphenyl)-3-hydroxy-3-methylbutanal (300661-16-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 84 percent / LiAlH₄ / tetrahydrofuran / 18 h / Heating

2.1: 82 percent / p-toluenesulfonic acid / 24 h / 20 °C

3.1: NaH / tetrahydrofuran

3.2: 91 percent / tetrabutylammonium iodide / tetrahydrofuran / 24 h

4.1: 92 percent / aq. H₂SO₄ / tetrahydrofuran / 4 h / 40 °C

5.1: 91 percent / Et₃N / CH₂Cl₂ / 0.17 h / -10 °C

6.1: 94 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 1 h / 20 °C

7.1: Mg; I₂ / tetrahydrofuran / 4 h / Heating

7.2: 92 percent / dilithium tetrachlorocuprate / tetrahydrofuran / -78 - -20 °C

8.1: 97 percent / H₂ / 10 percent Pd/C / methanol / 12 h

9.1: 90 percent / 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one / CH₂Cl₂; H₂O / 6 h / 20 °C

With lithium aluminium tetrahydride; sulfuric acid; hydrogen; iodine; sodium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; magnesium; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; 1.1: Reduction / 2.1: cyclocondensation / 3.1: deprotonation / 3.2: benzylation / 4.1: Hydrolysis / 5.1: Esterification / 6.1: cyclocondensation / 7.1: Metallation / 7.2: Ring cleavage / 8.1: Hydrogenolysis / 9.1: Oxidation;

DOI:10.1071/CH99091

upstream raw materials:

(S)-4-(2',5'-dimethoxyphenyl)-3-methylbutane-1,3-diol

(R)-(-)-citramalic acid

(R)-(+)-2-Methylbutane-1,2,4-triol

(R)-dimethyl 2-hydroxy-2-methylsuccinate

Refernces