[(1S,5R)-5-hydroxy-2,6,6-trimethylcyclohex-2-enyl]methyl 4-bromobenzoate

Base Information

• Chemical Name: [(1S,5R)-5-hydroxy-2,6,6-trimethylcyclohex-2-enyl]methyl 4-bromobenzoate
• CAS No.: 815581-77-2
• Molecular Formula: C₁₇H₂₁BrO₃
• Molecular Weight: 353.256
• Mol file: 815581-77-2.mol

Synonyms:[(1S,5R)-5-hydroxy-2,6,6-trimethylcyclohex-2-enyl]methyl 4-bromobenzoate

Chemical Property of [(1S,5R)-5-hydroxy-2,6,6-trimethylcyclohex-2-enyl]methyl 4-bromobenzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(1S,5R)-5-hydroxy-2,6,6-trimethylcyclohex-2-enyl]methyl 4-bromobenzoate

There total 3 articles about [(1S,5R)-5-hydroxy-2,6,6-trimethylcyclohex-2-enyl]methyl 4-bromobenzoate 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: 84.0%

4-chlorobenzoyl chloride (586-75-4) + (1S,5R)-5-(hydroxymethyl)-4,6,6-trimethylcyclohex-3-enol (815581-75-0) → [(1S,5R)-5-hydroxy-2,6,6-trimethylcyclohex-2-enyl]methyl 4-bromobenzoate (815581-77-2)

Guidance literature:

With triethylamine; In dichloromethane; at -40 - -20 ℃;

DOI:10.1021/jo049012j

Reference yield:

essigsaeure-<(E,R)-6,7-dihydroxy-3,7-dimethyl-2-octenyl>ester (86561-84-4) → [(1S,5R)-5-hydroxy-2,6,6-trimethylcyclohex-2-enyl]methyl 4-bromobenzoate (815581-77-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: MsCl; pyridine / CH₂Cl₂ / 22 °C

1.2: 80 percent / K₂CO₃ / methanol / 0 °C

2.1: 53 percent / ZrCl₄ / CH₂Cl₂ / 0.17 h / 22 °C

3.1: 84 percent / Et₃N / CH₂Cl₂ / -40 - -20 °C

With pyridine; zirconium(IV) chloride; methanesulfonyl chloride; triethylamine; In dichloromethane;

DOI:10.1021/jo049012j

Reference yield:

(S,E)-5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-en-1-ol (86561-83-3) → [(1S,5R)-5-hydroxy-2,6,6-trimethylcyclohex-2-enyl]methyl 4-bromobenzoate (815581-77-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 53 percent / ZrCl₄ / CH₂Cl₂ / 0.17 h / 22 °C

2: 84 percent / Et₃N / CH₂Cl₂ / -40 - -20 °C

With zirconium(IV) chloride; triethylamine; In dichloromethane;

DOI:10.1021/jo049012j

upstream raw materials:

4-chlorobenzoyl chloride

(1S,5R)-5-(hydroxymethyl)-4,6,6-trimethylcyclohex-3-enol

essigsaeure-<(E,R)-6,7-dihydroxy-3,7-dimethyl-2-octenyl>ester

(S,E)-5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-en-1-ol

Downstream raw materials:

4-Bromo-benzoic acid (1R,5S)-5-methanesulfonyloxy-2,6,6-trimethyl-cyclohex-2-enylmethyl ester

1-[((S)-2,6,6-trimethylcyclohex-2-enyl)methylsulfonyl]benzene

[(R)-2,6,6-trimethylcyclohexa-2,4-dienyl]methyl 4-bromobenzoate

tert-Butyl-[(E)-(S)-1-methyl-3-((S)-2,6,6-trimethyl-cyclohex-2-enyl)-allyloxy]-diphenyl-silane