1,3-Butanediol, 2-[2-[(1S,2S)-2-hydroxy-2,6,6-trimethylcyclohexyl]ethyl]-, 1-(4-methylbenzenesulfonate)

Base Information

• Chemical Name: 1,3-Butanediol, 2-[2-[(1S,2S)-2-hydroxy-2,6,6-trimethylcyclohexyl]ethyl]-, 1-(4-methylbenzenesulfonate)
• CAS No.: 680218-17-1
• Molecular Formula: C22H36O5S
• Molecular Weight: 412.591
• Mol file: 680218-17-1.mol

Synonyms:

Chemical Property of 1,3-Butanediol, 2-[2-[(1S,2S)-2-hydroxy-2,6,6-trimethylcyclohexyl]ethyl]-, 1-(4-methylbenzenesulfonate)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,3-Butanediol, 2-[2-[(1S,2S)-2-hydroxy-2,6,6-trimethylcyclohexyl]ethyl]-, 1-(4-methylbenzenesulfonate)

There total 6 articles about 1,3-Butanediol, 2-[2-[(1S,2S)-2-hydroxy-2,6,6-trimethylcyclohexyl]ethyl]-, 1-(4-methylbenzenesulfonate) 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: 62.0%

p-toluenesulfonyl chloride (98-59-9) + 2-[2-((1S,2S)-2-hydroxy-2,6,6-trimethylcyclohexyl)ethyl]butane-1,3-diol (680218-15-9) → 2-[2-((1S,2S)-2-hydroxy-2,6,6-trimethylcyclohexyl)ethyl]-3-hydroxybutyl 4-methylbenzenesulfonate (680218-17-1)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 13h;

DOI:10.1081/SCC-120027252

Reference yield:

(-)-(4aS,8aS)-3,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethylnaphthalen-1(2H)-one (60134-39-6) → 2-[2-((1S,2S)-2-hydroxy-2,6,6-trimethylcyclohexyl)ethyl]-3-hydroxybutyl 4-methylbenzenesulfonate (680218-17-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 93 percent / m-chloroperoxybenzoic acid; NaHCO₃ / CH₂Cl₂ / 1.5 h / 20 °C

2: sodium hydroxide / ethanol; H₂O / 2.3 h / 20 °C

3: 97 mg / diethyl ether / 0 °C

4: 74 percent / lithium diisopropylamide; hexamethylphosphoramide / tetrahydrofuran / 2.5 h / -78 °C

5: 97 percent / lithium aluminum hydride / diethyl ether / 2 h / 0 °C

6: 62 percent / triethylamine / CH₂Cl₂ / 13 h / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; lithium aluminium tetrahydride; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; 1: Baeyer-Villiger reaction / 4: aldol condensation;

DOI:10.1081/SCC-120027252

Reference yield:

(1S,7S)-1,8,8-trimethyl-2-oxabicyclo[5.4.0]undecan-3-one (217467-50-0) → 2-[2-((1S,2S)-2-hydroxy-2,6,6-trimethylcyclohexyl)ethyl]-3-hydroxybutyl 4-methylbenzenesulfonate (680218-17-1)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium hydroxide / ethanol; H₂O / 2.3 h / 20 °C

2: 97 mg / diethyl ether / 0 °C

3: 74 percent / lithium diisopropylamide; hexamethylphosphoramide / tetrahydrofuran / 2.5 h / -78 °C

4: 97 percent / lithium aluminum hydride / diethyl ether / 2 h / 0 °C

5: 62 percent / triethylamine / CH₂Cl₂ / 13 h / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; lithium aluminium tetrahydride; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; 3: aldol condensation;

DOI:10.1081/SCC-120027252

upstream raw materials:

p-toluenesulfonyl chloride

2-[2-((1S,2S)-2-hydroxy-2,6,6-trimethylcyclohexyl)ethyl]butane-1,3-diol

(-)-(4aS,8aS)-3,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethylnaphthalen-1(2H)-one

(1S,7S)-1,8,8-trimethyl-2-oxabicyclo[5.4.0]undecan-3-one

Downstream raw materials:

2-[2-((1S,2S)-2-hydroxy-2,6,6-trimethylcyclohexyl)ethyl]-3-oxobutyl 4-methylbenzenesulfonate

3-[2-((2S)-2-hydroxy-2,6,6-trimethylcyclohexyl)ethyl]but-3-en-2-one