Tert-butyl 2-hydroxybutanoate

Base Information

• Chemical Name: Tert-butyl 2-hydroxybutanoate
• CAS No.: 110171-06-7
• Molecular Formula: C8H16 O3
• Molecular Weight: 160.213
• Hs Code.: 2918199090
• European Community (EC) Number: 829-903-5
• Mol file: 110171-06-7.mol

Synonyms:tert-butyl (3R)-3-hydroxybutanoate;Tert-butyl 2-hydroxybutanoate;SCHEMBL473223;AKOS032961396;(+)-tert-Butyl (R)-2-hydroxybutyrate;FT-0693973;FT-0693975

Chemical Property of Tert-butyl 2-hydroxybutanoate

Chemical Property:

• Melting Point: 50-54 °C
• Boiling Point: 84 °C(Press: 0.1 Torr)
• PKA: 14.40±0.20(Predicted)
• PSA: 46.53000
• Density: 0.988±0.06 g/cm3(Predicted)
• LogP: 1.09900
• Storage Temp.: 2-8°C
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 160.109944368
• Heavy Atom Count: 11
• Complexity: 135

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Tert-butyl 2-hydroxybutanoate

There total 13 articles about Tert-butyl 2-hydroxybutanoate 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: 100.0%

tert-butyl acetoacetate (1694-31-1) → tert-butyl (R)-3-hydroxybutanoate (110171-06-7)

Guidance literature:

With hydrogen; C₅₀H₄₄Cl₂N₂O₈P₄Ru^(4-)*Zr⁽⁴⁺⁾; In methanol; at 20 ℃; for 20h; under 72402.6 Torr; Product distribution / selectivity;

Reference yield: 100.0%

tert-butyl acetoacetate (1694-31-1) → tert-butyl (S)-3-hydroxybutyrate (82578-45-8) + tert-butyl (R)-3-hydroxybutanoate (110171-06-7)

Guidance literature:

With hydrogen; C₅₀H₄₄Cl₂N₂O₈P₄Ru^(4-)*Zr⁽⁴⁺⁾; In methanol; at 20 ℃; for 20h; under 72402.6 Torr; Product distribution / selectivity;

Reference yield: 97.0%

tert-butyl acetoacetate (1694-31-1) → Methyl (R)-3-hydroxybutyrate (3976-69-0) + tert-butyl (R)-3-hydroxybutanoate (110171-06-7)

Guidance literature:

With hydrogenchloride; hydrogen; [RuCl₂-((R)-binap)]*NEt₃; In methanol; at 40 ℃; for 8h; under 2585.7 Torr; Kinetics; effect of acid, other substrate;

DOI:10.1021/jo00051a002

upstream raw materials:

tert-butyl acetoacetate

3-Acetoxy-butyric acid tert-butyl ester

(+)<3(S),S(R)> tert-butyl 3-hydroxy-4-(p-tolylsulfinyl)butyrate

(R)-3-(benzyloxy)butanoic acid-(tert-butyl)ester

Downstream raw materials:

(E)-(2R,3S)-2-((R)-1-Hydroxy-ethyl)-3-methoxycarbonylamino-5-phenyl-pent-4-enoic acid tert-butyl ester

(E)-(2R,3R)-2-((R)-1-Hydroxy-ethyl)-3-methoxycarbonylamino-5-phenyl-pent-4-enoic acid tert-butyl ester

(E)-(2R,3R)-2-((R)-1-Hydroxy-ethyl)-3-methoxycarbonylamino-5-phenylsulfanyl-pent-4-enoic acid tert-butyl ester

(E)-(2R,3S)-2-((R)-1-Hydroxy-ethyl)-3-methoxycarbonylamino-5-phenylsulfanyl-pent-4-enoic acid tert-butyl ester

Refernces

• 1、 Lam, Kim Hung,Xu, Lijin,Feng, Lichun,Ruan, Jiwu,Fan, Qinghua,Chan, Albert S.C.. "Ruthenium catalyzed asymmetric hydrogenation of α- and β-keto esters in ionic liquids using chiral P-Phos ligand". . p. 903 - 908. Retrieved 2005.
• 2、 Wang, Peiyuan,Liu, Xiao,Yang, Jie,Yang, Yan,Zhang, Lei,Yang, Qihua,Li, Can. "Chirally functionalized mesoporous organosilicas with built-in BINAP ligand for asymmetric catalysis". . p. 8009 - 8014. Retrieved 2009.
• 3、 Everacre, Kathelyne,Mortreux, André,Carpentier, Jean-Fran?ois. "Ruthenium(II)-Catalyzed Asymmetric Transfer Hydrogenation of Carbonyl Compounds with 2-Propanol and Ephedrine-Type Ligands". . p. 67 - 77. Retrieved 2003.
• 4、 King, Steven A.,Thompson, Andrew S.,King, Anthony O.,Verhoeven, Thomas R.. "An Improved Procedure for the Synthesis and Use of 2*NEt3. Dependence of the Ru(II)-BINAP Catalyzed Asymmetric Hydrogenation of β-Keto Esters on Trace Amounts of Acid". . p. 6689 - 6691. Retrieved 1992.
• 5、 De Souza Ramos, Aline,Ribeiro, Joyce Benzaquem,De Oliveira Lopes, Raquel,De Souza, Rodrigo Octavio Mendonca Alves. "Whole cells in enantioselective reduction of tert-butyl acetoacetate". . p. 1611 - 1618. Retrieved 2013.
• 6、 Scilimati, A.,Ngooi, T. K.,Sih, Charles J.. "BIOCATALYTIC RESOLUTION OF (+/-)-HYDROXYALKANOIC ESTERS. A STRATEGY FOR ENHANCING THE ENANTIOMERIC SPECIFICITY OF LIPASE-CATALYZED ESTER HYDROLYSIS.". . p. 4927 - 4930. Retrieved 1988.
• 7、 Wang, Xu,Lu, Sheng-Mei,Li, Jun,Liu, Yan,Li, Can. "Conjugated microporous polymers with chiral BINAP ligand built-in as efficient catalysts for asymmetric hydrogenation". . p. 2585 - 2589. Retrieved 2015.
• 8、 Zhou, Hai-Feng,Fan, Qing-Hua,Tang, Wei-Jun,Xu, Li-Jin,He, Yan-Mei,Deng, Guo-Jun,Zhao, Li-Wen,Gu, Lian-Quan,Chan, Albert S. C.. "Polyethylene glycol as an environmentally friendly and recyclable reaction medium for enantioselective hydrogenation". . p. 2172 - 2182. Retrieved 2006.
• 9、 Pye, Philip J.,Rossen, Kai,Reamer, Robert A.,Volante,Reider, Paul J.. "[2.2]PHANEPHOS-ruthenium(II) complexes: Highly active asymmetric catalysts for the hydrogenation of β-ketoesters". . p. 4441 - 4444. Retrieved 1998.
• 10、 Wang, Tao,Lyu, Yuan,Xiong, Kai,Wang, Wenlong,Zhang, Hao,Zhan, Zhuangping,Jiang, Zheng,Ding, Yunjie. "Chiral BINAP-based hierarchical porous polymers as platforms for efficient heterogeneous asymmetric catalysis". . p. 890 - 897. Retrieved 2017.