4-<2,6,6-trimethyl 5-(4-hydroxy 3-methyl 2E-butenyl) 1-cyclohexenyl> 3E-buten 2-one (2-hydroxyprenyl β-ionone)

Base Information

• Chemical Name: 4-<2,6,6-trimethyl 5-(4-hydroxy 3-methyl 2E-butenyl) 1-cyclohexenyl> 3E-buten 2-one (2-hydroxyprenyl β-ionone)
• CAS No.: 99647-25-3
• Molecular Formula: C₁₈H₂₈O₂
• Molecular Weight: 276.419
• Mol file: 99647-25-3.mol

Synonyms:

Chemical Property of 4-<2,6,6-trimethyl 5-(4-hydroxy 3-methyl 2E-butenyl) 1-cyclohexenyl> 3E-buten 2-one (2-hydroxyprenyl β-ionone)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-<2,6,6-trimethyl 5-(4-hydroxy 3-methyl 2E-butenyl) 1-cyclohexenyl> 3E-buten 2-one (2-hydroxyprenyl β-ionone)

There total 3 articles about 4-<2,6,6-trimethyl 5-(4-hydroxy 3-methyl 2E-butenyl) 1-cyclohexenyl> 3E-buten 2-one (2-hydroxyprenyl β-ionone) 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:

pseudoionone (141-10-6,3548-78-5) + isoprene epoxide (1838-94-4) → All E 6,12-dimethyl 13-hydroxy 9-isopropenyl 3,5,11-tridecatrien 2-one (hydroxyprenyl pseudoionone) (99647-38-8) + 4-<2,6,6-trimethyl 5-(4-hydroxy 3-methyl 2E-butenyl) 1-cyclohexenyl> 3E-buten 2-one (2-hydroxyprenyl β-ionone) (99647-25-3) + 4α-<2,6,6-trimethyl 5β-(4-hydroxy 3-methyl 2E-butenyl) 2-cyclohexenyl> 3E-buten 2-one (2-hydroxyprenyl α-trans ionone) (99647-24-2,99685-15-1) + 4β-<2,6,6-trimethyl 5β-(4-hydroxy 3-methyl 2E-butenyl) 2-cyclohexenyl> 3E-buten 2-one (2-hydroxyprenyl α-cis-ionone) (99647-24-2,99685-15-1)

Guidance literature:

With zinc(II) chloride; In nitromethane; at -15 ℃; for 0.75h; Yield given. Further byproducts given. Yields of byproduct given;

DOI:10.1016/S0040-4020(01)96529-9

Reference yield:

pseudoionone (141-10-6,3548-78-5) + isoprene epoxide (1838-94-4) → 4-<2,6,6-trimethyl 5-(4-hydroxy 3-methyl 2E-butenyl) 1-cyclohexenyl> 3E-buten 2-one (2-hydroxyprenyl β-ionone) (99647-25-3) + 4-<2-chloro 2,6,6-trimethyl 5-(4-hydroxy 3-methyl 2E-butenyl) cyclohexyl> 3E-buten 2-one (2-hydroxyprenyl hydrochloroionone) (99647-26-4) + 4α-<2,6,6-trimethyl 5β-(4-hydroxy 3-methyl 2E-butenyl) 2-cyclohexenyl> 3E-buten 2-one (2-hydroxyprenyl α-trans ionone) (99647-24-2,99685-15-1) + 4β-<2,6,6-trimethyl 5β-(4-hydroxy 3-methyl 2E-butenyl) 2-cyclohexenyl> 3E-buten 2-one (2-hydroxyprenyl α-cis-ionone) (99647-24-2,99685-15-1)

Guidance literature:

With zinc(II) chloride; In nitromethane; at -15 ℃; for 0.75h; Yield given. Further byproducts given. Yields of byproduct given;

DOI:10.1016/S0040-4020(01)96529-9

Reference yield:

pseudoionone (141-10-6,3548-78-5) + isoprene epoxide (1838-94-4) → 4-<2,6,6-trimethyl 5-(4-hydroxy 3-methyl 2E-butenyl) 1-cyclohexenyl> 3E-buten 2-one (2-hydroxyprenyl β-ionone) (99647-25-3) + 4α-<2,6,6-trimethyl 5β-(4-hydroxy 3-methyl 2E-butenyl) 2-cyclohexenyl> 3E-buten 2-one (2-hydroxyprenyl α-trans ionone) (99647-24-2,99685-15-1) + 4β-<2,6,6-trimethyl 5β-(4-hydroxy 3-methyl 2E-butenyl) 2-cyclohexenyl> 3E-buten 2-one (2-hydroxyprenyl α-cis-ionone) (99647-24-2,99685-15-1)

Guidance literature:

With zinc(II) chloride; In methylamine; at -15 ℃; for 2h; Product distribution; investigation of the effect of Lewis acid promotors, temperature, stereochemistry of starting compound on the stereochemical outcome of the reaction;

DOI:10.1016/S0040-4020(01)96529-9

upstream raw materials:

pseudoionone

isoprene epoxide

Downstream raw materials:

All E, C_.p. 450

C_.p. 450, Z-isomer

3-methyl 5-<2,6,6-trimethyl 5-(4-hydroxy 3-methyl 2E-butenyl) 1-cylohexenyl> 2,4-pentadienyl triphenylphosphonium bromide (2-hydroxyprenyl β-ionylidene ethyltriphenylphosphonium bromide)

3-methyl 5-<2,6,6-trimetyl 5-(4-hydroxy 3-methyl 2E-butenyl) 2-cyclohexenyl> 1,4-pentadien 3-ol (2-hydroxyprenyl vinyl β-ionol)