3-Cyclopentene-1-acetaldehyde, 2,2-dimethyl-3-[2-[[(4-methylphenyl)sulfonyl]oxy]ethyl]-, (R)-

Base Information

• Chemical Name: 3-Cyclopentene-1-acetaldehyde, 2,2-dimethyl-3-[2-[[(4-methylphenyl)sulfonyl]oxy]ethyl]-, (R)-
• CAS No.: 144342-07-4
• Molecular Formula: C18H24O4S
• Molecular Weight: 336.452
• Mol file: 144342-07-4.mol

Synonyms:

Chemical Property of 3-Cyclopentene-1-acetaldehyde, 2,2-dimethyl-3-[2-[[(4-methylphenyl)sulfonyl]oxy]ethyl]-, (R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-Cyclopentene-1-acetaldehyde, 2,2-dimethyl-3-[2-[[(4-methylphenyl)sulfonyl]oxy]ethyl]-, (R)-

There total 8 articles about 3-Cyclopentene-1-acetaldehyde, 2,2-dimethyl-3-[2-[[(4-methylphenyl)sulfonyl]oxy]ethyl]-, (R)- 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: 87.0%

(+)-(1R)-3-(2-Hydroxyethyl)-2,2-dimethylcyclopent-3-ene-1-acetaldehyde (144342-04-1) + p-toluenesulfonyl chloride (98-59-9) → (+)-(4R)-5,5-Dimethyl-4-(2-oxoethyl)cyclopent-1-ene-1-ethyl 4-toluenesulfonate (144342-07-4)

Guidance literature:

With pyridine; at -10 ℃;

DOI:10.1002/hlca.19920750507

Reference yield:

(1R)-nopol tosylate (81600-63-7) → (+)-(4R)-5,5-Dimethyl-4-(2-oxoethyl)cyclopent-1-ene-1-ethyl 4-toluenesulfonate (144342-07-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 93 percent / EtMgI / diethyl ether / 1 h / Ambient temperature

2: 13 percent / 40 percent peracetic acid, Na₂CO₃, EDTA tetrasodium salt / toluene / Ambient temperature

3: 83 percent / 40 percent peracetic acid/AcOH, Na₂CO₃, EDTA tetrasodium salt / toluene / Ambient temperature

4: 69 percent / ZnBr₂ / toluene / Heating

5: 80 percent / LiOH*H₂O / tetrahydrofuran; H₂O / 48 h / Ambient temperature

6: 87 percent / pyridine / -10 °C

With pyridine; ethylmagnesium iodide; peracetic acid; lithium hydroxide; ethylene diamine tetraacetic acid tetrasodium salt; sodium carbonate; acetic acid; zinc dibromide; In tetrahydrofuran; diethyl ether; water; toluene;

DOI:10.1002/hlca.19920750507

Reference yield:

(-)-(1R)-2-(2-Iodoethyl)-6,6-dimethylbicyclo<3.1.1>hept-2-ene (144342-18-7) → (+)-(4R)-5,5-Dimethyl-4-(2-oxoethyl)cyclopent-1-ene-1-ethyl 4-toluenesulfonate (144342-07-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 13 percent / 40 percent peracetic acid, Na₂CO₃, EDTA tetrasodium salt / toluene / Ambient temperature

2: 83 percent / 40 percent peracetic acid/AcOH, Na₂CO₃, EDTA tetrasodium salt / toluene / Ambient temperature

3: 69 percent / ZnBr₂ / toluene / Heating

4: 80 percent / LiOH*H₂O / tetrahydrofuran; H₂O / 48 h / Ambient temperature

5: 87 percent / pyridine / -10 °C

With pyridine; peracetic acid; lithium hydroxide; ethylene diamine tetraacetic acid tetrasodium salt; sodium carbonate; acetic acid; zinc dibromide; In tetrahydrofuran; water; toluene;

DOI:10.1002/hlca.19920750507

upstream raw materials:

(+)-(1R)-3-(2-Hydroxyethyl)-2,2-dimethylcyclopent-3-ene-1-acetaldehyde

p-toluenesulfonyl chloride

(1R)-nopol tosylate

(1R)-(-)-nopol

Refernces