(3S)-2-hydroxy-3-methyl-3-(4-methylphenyl)tetrahydrofuran

Base Information

• Chemical Name: (3S)-2-hydroxy-3-methyl-3-(4-methylphenyl)tetrahydrofuran
• CAS No.: 105556-92-1
• Molecular Formula: C₁₂H₁₆O₂
• Molecular Weight: 192.258
• Mol file: 105556-92-1.mol

Synonyms:

Chemical Property of (3S)-2-hydroxy-3-methyl-3-(4-methylphenyl)tetrahydrofuran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S)-2-hydroxy-3-methyl-3-(4-methylphenyl)tetrahydrofuran

There total 12 articles about (3S)-2-hydroxy-3-methyl-3-(4-methylphenyl)tetrahydrofuran 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: 98.0%

(S)-(-)-2-methyl-2-(4-methylphenyl)-4-butanolide (141116-74-7) → (3S)-2-hydroxy-3-methyl-3-(4-methylphenyl)tetrahydrofuran (105556-92-1,141045-48-9,141045-49-0)

Guidance literature:

With diisobutylaluminium hydride; In toluene; at -78 ℃; for 0.166667h;

DOI:10.1021/jo00038a041

Reference yield: 91.3%

(3R)-4,4-ethylenedioxy-3-methyl-3-p-tolylbutan-1-ol (105556-90-9) → (2S)-2-hydroxy-3-methyl-3-p-tolyltetrahydrofuran (105556-92-1,141045-48-9,141045-49-0)

Guidance literature:

With toluene-4-sulfonic acid; In water; acetone; at 45 - 50 ℃; for 15h;

DOI:10.1248/cpb.33.4821

Reference yield:

methyl 2-(4-methylphenyl)propanoate (79443-97-3) → (3S)-2-hydroxy-3-methyl-3-(4-methylphenyl)tetrahydrofuran (105556-92-1,141045-48-9,141045-49-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 1) i-Pr₂NH, n-BuLi / 1) THF, -78 deg C, 1 h, 2) 0 deg C, 30 min

2: 95 percent / 2N NaOH / H₂O / 1 h / 25 °C / pig liver esterase, pH 7.2

3: 95 percent / oxalyl chloride / benzene / 12 h / 45 °C

4: 80 percent / diethyl ether / 0.25 h / 0 °C

5: 6 N HCl / tetrahydrofuran / 12 h / 20 °C

6: 80 percent / 10percent BF₃*Et₂O / CH₂Cl₂ / 24 h / Ambient temperature

7: 64 percent / Raney nickel (W₂) / ethanol / 24 h / Heating

8: 98 percent / diisobutylaluminiumhydride (DIBALH) / toluene / 0.17 h / -78 °C

With hydrogenchloride; sodium hydroxide; n-butyllithium; oxalyl dichloride; Raney Nickel (W₂); boron trifluoride diethyl etherate; diisobutylaluminium hydride; diisopropylamine; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; toluene; benzene;

DOI:10.1021/jo00038a041

upstream raw materials:

(3R)-4,4-ethylenedioxy-3-methyl-3-p-tolylbutan-1-ol

(2R)-2-methyl-2-p-tolyl-3-butenal

(3R)-4,4-ethylenedioxy-3-methyl-3-p-tolylbut-1-ene

(S)-(-)-2-methyl-2-(4-methylphenyl)-4-butanolide

Downstream raw materials:

(3S)-(+)-3-methyl-3-(4-methylphenyl)pentane-1,4-diol

(3S)-(-)-3-methyl-3-(4-methylphenyl)pentane-1,4-diol

(3S)-3-methyl-3-p-tolyl-4-pentenal

(3S)-3-methyl-3-p-tolyl-4-pentenol