Methyl 2-hydroxy-3,3-dimethylbutanoate

Base Information

• Chemical Name: Methyl 2-hydroxy-3,3-dimethylbutanoate
• CAS No.: 121129-31-5
• Molecular Formula: C7H14O3
• Molecular Weight: 146.186
• European Community (EC) Number: 818-435-7
• Nikkaji Number: J344.011G
• Mol file: 121129-31-5.mol

Synonyms:Methyl 2-hydroxy-3,3-dimethylbutanoate;121129-31-5;SCHEMBL9370544;YYAKMBGOMGURAY-UHFFFAOYSA-N;methyl 2-hydroxy-3,3-dimethybutyrate;AKOS011496312;Methyl2-hydroxy-3,3-dimethylbutanoate;BS-52503;CS-0311804;E82662;EN300-130373;methyl (+/-)-2-hydroxy-3,3-dimethylbutanoate;2-Hydroxy-3,3-dimethylbutyric acid methyl ester;Z965047812

Chemical Property of Methyl 2-hydroxy-3,3-dimethylbutanoate

Chemical Property:

• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 146.094294304
• Heavy Atom Count: 10
• Complexity: 123

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)C(C(=O)OC)O

Technology Process of Methyl 2-hydroxy-3,3-dimethylbutanoate

There total 8 articles about Methyl 2-hydroxy-3,3-dimethylbutanoate 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: 99.0%

methanol (67-56-1) + 2-hydroxy-3,3-dimethylbutanoic acid (4026-20-4,851866-86-9) → (+/-)-methyl (2-hydroxy-3,3-dimethyl)butyrate (121129-31-5)

Guidance literature:

With acetyl chloride; at 65 ℃; for 4h; Inert atmosphere; Schlenk technique;

DOI:10.1021/ja411772n

Reference yield:

3,3-dimethyl-2-trifluoromethanesulfonyloxy-butyric acid methyl ester → Methyl 2,3-dimethyl-2-butenoate (49714-66-1) + (+/-)-methyl (2-hydroxy-3,3-dimethyl)butyrate (121129-31-5) + methyl trimethylpyruvate (38941-46-7) + methyl 2,3-dimethylbut-3-enoate (49714-67-2)

Guidance literature:

With 2,6-dimethylpyridine; In dimethylsulfoxide-d6; at 25 ℃; Further Variations:; Solvents; Kinetics; Product distribution;

DOI:10.1021/jo0356558

Reference yield:

3,3-dimethyl-butan-2-one (75-97-8) → (+/-)-methyl (2-hydroxy-3,3-dimethyl)butyrate (121129-31-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydroxide; potassium permanganate / water / 16.5 h / 0 - 20 °C / Inert atmosphere; Schlenk technique

1.2: Cooling; Inert atmosphere; Schlenk technique

2.1: sodium hydroxide; sodium tetrahydroborate / water / 16.5 h / 0 - 20 °C / Inert atmosphere; Schlenk technique

2.2: Inert atmosphere; Schlenk technique

3.1: acetyl chloride / 4 h / 65 °C / Inert atmosphere; Schlenk technique

With sodium tetrahydroborate; potassium permanganate; acetyl chloride; sodium hydroxide; In water;

DOI:10.1021/ja411772n

upstream raw materials:

(+/-)-2-hydroxy-2,3-dimethylbutanoic acid

dimethyl sulfate

diazomethane

2-hydroxy-3,3-dimethylbutanoic acid

Downstream raw materials:

methyl (R)-2-hydroxy-3,3-dimethylbutanoate

methyl 2-[(2,6-dichlorobenzyl)oxy]-3,3-dimethylbutanoate

methyl 2-(benzyloxy)-3,3-dimethylbutanoate

9-(tert-butyl)-12-(4-methoxyphenyl)-8-oxaspiro[5.6]dodeca-9,11-dien-7-one