Butanedioic acid, 2-methyl-2-(4-methylphenyl)-, dimethyl ester, (S)-

Base Information

• Chemical Name: Butanedioic acid, 2-methyl-2-(4-methylphenyl)-, dimethyl ester, (S)-
• CAS No.: 124909-09-7
• Molecular Formula: C₁₄H₁₈O₄
• Molecular Weight: 250.295
• Mol file: 124909-09-7.mol

Synonyms:

Chemical Property of Butanedioic acid, 2-methyl-2-(4-methylphenyl)-, dimethyl ester, (S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Butanedioic acid, 2-methyl-2-(4-methylphenyl)-, dimethyl ester, (S)-

There total 11 articles about Butanedioic acid, 2-methyl-2-(4-methylphenyl)-, dimethyl ester, (S)- 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: 14.0%

methanol (67-56-1) + (R)-(+)-methyl 4-diazo-2-methyl-2-(4-methylphenyl)-3-oxobutanoate (133678-80-5) → methyl 2-(4-methylphenyl)propanoate (79443-97-3) + (S)-(+)-dimethyl 2-methyl-2-(4-methylphenyl)succinate (124909-09-7) + (+/-)-methyl 2-<2-<(methoxycarbonyl)methyl>-4-methylphenyl>propionate (141045-36-5)

Guidance literature:

With triethylamine; silver benzoate; for 3h; Heating;

DOI:10.1021/jo00038a041

Reference yield:

methyl 2-(4-methylphenyl)propanoate (79443-97-3) → (S)-(+)-dimethyl 2-methyl-2-(4-methylphenyl)succinate (124909-09-7)

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: Et₃N / tetrahydrofuran / 1 h / Ambient temperature

4: NaBH₄ / methanol / 1 h / Ambient temperature

5: 90 percent / pyridine / CHCl₃ / 48 h / 4 °C

6: H₂O / dimethylsulfoxide / 12 h / 100 °C

7: 1) 10 N HCl; 2) KOH / 1) 100 deg C, 14 h; 2) ethylene glycol, reflux, 14 h

8: diethyl ether / 0.08 h / 20 °C

With pyridine; hydrogenchloride; potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; water; triethylamine; diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; chloroform; water; dimethyl sulfoxide;

DOI:10.1021/jo00038a041

Reference yield:

dimethyl 2-methyl-2-(4-methylphenyl)malonate (127047-04-5) → (S)-(+)-dimethyl 2-methyl-2-(4-methylphenyl)succinate (124909-09-7)

Guidance literature:

Multi-step reaction with 7 steps

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

2: Et₃N / tetrahydrofuran / 1 h / Ambient temperature

3: NaBH₄ / methanol / 1 h / Ambient temperature

4: 90 percent / pyridine / CHCl₃ / 48 h / 4 °C

5: H₂O / dimethylsulfoxide / 12 h / 100 °C

6: 1) 10 N HCl; 2) KOH / 1) 100 deg C, 14 h; 2) ethylene glycol, reflux, 14 h

7: diethyl ether / 0.08 h / 20 °C

With pyridine; hydrogenchloride; potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; water; triethylamine; In tetrahydrofuran; methanol; diethyl ether; chloroform; water; dimethyl sulfoxide;

DOI:10.1021/jo00038a041

upstream raw materials:

diazomethane

(S)-(+)-2-methyl-2-(4-methylphenyl)butanedioic acid

methanol

(R)-(+)-methyl 4-diazo-2-methyl-2-(4-methylphenyl)-3-oxobutanoate

Downstream raw materials:

dimethyl-2,3,3-trimethyl-2-(4-methylphenyl)succinate

(S)-2,3-Dimethyl-2-p-tolyl-succinic acid dimethyl ester