(Z)-5-Hydroxymethyl-1-[2-(1-methylcyclohexa-2,5-dien-1-yl)ethenyl]-2,6,6-trimethylcyclohex-1-ene

Base Information

Chemical Name:(Z)-5-Hydroxymethyl-1-[2-(1-methylcyclohexa-2,5-dien-1-yl)ethenyl]-2,6,6-trimethylcyclohex-1-ene
CAS No.:318949-71-2
Molecular Formula:C₁₉H₂₈O
Molecular Weight:272.431
Hs Code.:

Synonyms:(Z)-5-Hydroxymethyl-1-[2-(1-methylcyclohexa-2,5-dien-1-yl)ethenyl]-2,6,6-trimethylcyclohex-1-ene

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Chemical Property of (Z)-5-Hydroxymethyl-1-[2-(1-methylcyclohexa-2,5-dien-1-yl)ethenyl]-2,6,6-trimethylcyclohex-1-ene

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Technology Process of (Z)-5-Hydroxymethyl-1-[2-(1-methylcyclohexa-2,5-dien-1-yl)ethenyl]-2,6,6-trimethylcyclohex-1-ene

There total 11 articles about (Z)-5-Hydroxymethyl-1-[2-(1-methylcyclohexa-2,5-dien-1-yl)ethenyl]-2,6,6-trimethylcyclohex-1-ene 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: 95.0%

: 318949-70-1
(Z)-5-tert-Butyldimethylsilyloxymethyl-1-[2-(1-methylcyclohexa-2,5-dien-1-yl)ethenyl]-2,6,6-trimethylcyclohex-1-ene

: 318949-71-2
(Z)-5-Hydroxymethyl-1-[2-(1-methylcyclohexa-2,5-dien-1-yl)ethenyl]-2,6,6-trimethylcyclohex-1-ene

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran;
DOI:10.1039/P19950002811

Reference yield:

: 171504-38-4
(E)-5-tert-butyldimethylsiloxymethyl-1-<2-(1-methyl-2,5-cyclohexadien-1-yl)-ethen-1-yl>-2,6,6-trimethyl-1-cyclohexene

: 318949-71-2
(Z)-5-Hydroxymethyl-1-[2-(1-methylcyclohexa-2,5-dien-1-yl)ethenyl]-2,6,6-trimethylcyclohex-1-ene

Guidance literature:: Multi-step reaction with 2 steps

1: 67 percent / 2-acetylnaphthalene / benzene / 3 h / 0 - 5 °C / Irradiation

2: 95 percent / Bu₄NF / tetrahydrofuran / 16 h / 20 °C

With tetrabutyl ammonium fluoride; methyl 2-naphthyl ketone; In tetrahydrofuran; benzene; 1: Isomerization / 2: Substitution;
DOI:10.1039/b005727o

Reference yield:

: 144067-40-3
Acetic acid 5-formyl-2,6,6-trimethyl-cyclohex-1-enylmethyl ester

: 318949-71-2
(Z)-5-Hydroxymethyl-1-[2-(1-methylcyclohexa-2,5-dien-1-yl)ethenyl]-2,6,6-trimethylcyclohex-1-ene

Guidance literature:: Multi-step reaction with 10 steps

1.1: NaBH₄ / methanol / 0 °C

2.1: DMAP; Et₃N / CH₂Cl₂ / 0 - 20 °C

3.1: DIBAL-H / diethyl ether / 0 °C

4.1: 95 percent / pyridine; Bu₃P / 9 h / 20 °C

5.1: oxone / tetrahydrofuran; methanol; H₂O / 4 h / 20 °C

6.1: DMAP; Et₃N / CH₂Cl₂ / 20 °C

7.1: LDA / tetrahydrofuran; hexane / 0.5 h / 0 °C

7.2: tetrahydrofuran; hexane / 1 h / -78 °C

8.1: 82 percent / SmI₂; HMPA / tetrahydrofuran / 0.5 h / 20 °C

9.1: 67 percent / 2-acetylnaphthalene / benzene / 3 h / 0 - 5 °C / Irradiation

10.1: 95 percent / Bu₄NF / tetrahydrofuran / 16 h / 20 °C

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; Oxone; sodium tetrahydroborate; samarium diiodide; tributylphosphine; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; triethylamine; methyl 2-naphthyl ketone; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; benzene; 1.1: Reduction / 2.1: Etherification / 3.1: Reduction / 4.1: Substitution / 5.1: Oxidation / 6.1: Etherification / 7.1: Metallation / 7.2: Substitution / 8.1: Elimination / 9.1: Isomerization / 10.1: Substitution;
DOI:10.1039/b005727o