Cyclopentanemethanol, 1,2-dimethyl-2-(4-methylphenyl)-, (1R,2R)-

Base Information

• Chemical Name: Cyclopentanemethanol, 1,2-dimethyl-2-(4-methylphenyl)-, (1R,2R)-
• CAS No.: 740800-48-0
• Molecular Formula: C15H22O
• Molecular Weight: 218.339
• DSSTox Substance ID: DTXSID70464039
• Nikkaji Number: J1.857.440C
• Wikidata: Q82289215
• Mol file: 740800-48-0.mol

Synonyms:740800-48-0;Cyclopentanemethanol, 1,2-dimethyl-2-(4-methylphenyl)-, (1R,2R)-;DTXSID70464039

Chemical Property of Cyclopentanemethanol, 1,2-dimethyl-2-(4-methylphenyl)-, (1R,2R)-

Chemical Property:

• XLogP3: 4.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 218.167065321
• Heavy Atom Count: 16
• Complexity: 242

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)C2(CCCC2(C)CO)C
• Isomeric SMILES: CC1=CC=C(C=C1)[C@]2(CCC[C@@]2(C)CO)C

Technology Process of Cyclopentanemethanol, 1,2-dimethyl-2-(4-methylphenyl)-, (1R,2R)-

There total 5 articles about Cyclopentanemethanol, 1,2-dimethyl-2-(4-methylphenyl)-, (1R,2R)- 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: 98.0%

(1R,2R,4S)-1,2-dimethyl-2-p-tolylcyclopentanecarboxylic acid ethyl ester (740800-47-9) → (1R,2R)-(1,2-dimethyl-2-p-tolyl-cyclopentyl)methanol (740800-48-0)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 0 - 20 ℃;

DOI:10.1016/j.tet.2004.05.037

Reference yield:

(+)-(1S,2S,4R)-4-hydroxy-2-methyl-2-p-tolylcyclopentanecarboxylic acid ethyl ester (613669-95-7) → (1R,2R)-(1,2-dimethyl-2-p-tolyl-cyclopentyl)methanol (740800-48-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 100 percent / imidazole / dimethylformamide / 1 h / 20 °C

2.1: LDA; HMPA / tetrahydrofuran; diethyl ether; hexane / 0.67 h / -90 °C

2.2: 93 percent / tetrahydrofuran; diethyl ether; hexane / -90 - 0 °C

3.1: 98 percent / TBAF / tetrahydrofuran / 4 h / 20 °C

4.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

4.2: 98 percent / tetrahydrofuran / 1 h

5.1: 96 percent / AIBN; Bu₃SnH / toluene / 0.67 h / Heating

6.1: 98 percent / LiAlH₄ / diethyl ether / 0 - 20 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium hydride; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.tet.2004.05.037

Reference yield:

(1R,2R,4S)-4-hydroxy-1,2-dimethyl-2-p-tolyl-cyclopentanecarboxylic acid ethyl ester (740800-45-7) → (1R,2R)-(1,2-dimethyl-2-p-tolyl-cyclopentyl)methanol (740800-48-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

1.2: 98 percent / tetrahydrofuran / 1 h

2.1: 96 percent / AIBN; Bu₃SnH / toluene / 0.67 h / Heating

3.1: 98 percent / LiAlH₄ / diethyl ether / 0 - 20 °C

With lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hydride; In tetrahydrofuran; diethyl ether; toluene;

DOI:10.1016/j.tet.2004.05.037

upstream raw materials:

(1R,2R,4S)-1,2-dimethyl-2-p-tolylcyclopentanecarboxylic acid ethyl ester

(+)-(1S,2S,4R)-4-hydroxy-2-methyl-2-p-tolylcyclopentanecarboxylic acid ethyl ester

(1R,2R,4S)-4-hydroxy-1,2-dimethyl-2-p-tolyl-cyclopentanecarboxylic acid ethyl ester

(1R,2R,4S)-1,2-dimethyl-4-methylsulfanylthiocarbonyloxy-2-p-tolyl-cyclopentanecarboxylic acid ethyl ester