(5-cyclohex-2-enylmethyl-5-hydroxy-6,6-dimethyl-cyclohex-1-enyl)-acetaldehyde

Base Information

• Chemical Name: (5-cyclohex-2-enylmethyl-5-hydroxy-6,6-dimethyl-cyclohex-1-enyl)-acetaldehyde
• CAS No.: 256469-35-9
• Molecular Formula: C₁₇H₂₆O₂
• Molecular Weight: 262.392
• Mol file: 256469-35-9.mol

Synonyms:(5-cyclohex-2-enylmethyl-5-hydroxy-6,6-dimethyl-cyclohex-1-enyl)-acetaldehyde

Chemical Property of (5-cyclohex-2-enylmethyl-5-hydroxy-6,6-dimethyl-cyclohex-1-enyl)-acetaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5-cyclohex-2-enylmethyl-5-hydroxy-6,6-dimethyl-cyclohex-1-enyl)-acetaldehyde

There total 8 articles about (5-cyclohex-2-enylmethyl-5-hydroxy-6,6-dimethyl-cyclohex-1-enyl)-acetaldehyde 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: 61.0%

1-cyclohex-2-enylmethyl-3-(2-hydroxy-ethyl)-2,2-dimethyl-cyclohex-3-enol (256469-32-6) → (5-cyclohex-2-enylmethyl-5-hydroxy-6,6-dimethyl-cyclohex-1-enyl)-acetaldehyde (256469-35-9)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -60 ℃; under 15 Torr;

DOI:10.1002/(SICI)1099-0690(199912)1999:12<3241::AID-EJOC3241>3.0.CO;2-9

Reference yield:

ethylene glycole monoacetal of 2,2-dimethylcyclohexane-1,3-dione (14782-52-6) → (5-cyclohex-2-enylmethyl-5-hydroxy-6,6-dimethyl-cyclohex-1-enyl)-acetaldehyde (256469-35-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 85 percent / LiHMDS / tetrahydrofuran / 3 h / 0 °C

2: 95 percent / LiCl; DBU / Pd(PPh₃)4 / tetrahydrofuran / 20 °C / Heating

3: 100 percent / 9-BBN; H₂O₂; NaOH / tetrahydrofuran; ethanol / 3 h / Heating

4: 99 percent / TsOH / tetrahydrofuran; H₂O / 18 h / Heating

5: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 15 h / 20 °C

6: 83 percent / Mg; CeCl₃ / tetrahydrofuran / 15 h / 0 - 20 °C

7: 71 percent / Bu₄NF / tetrahydrofuran / 15 h / 0 - 20 °C

8: 61 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -60 °C / 15 Torr

With dmap; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; cerium(III) chloride; oxalyl dichloride; tetrabutyl ammonium fluoride; dihydrogen peroxide; toluene-4-sulfonic acid; magnesium; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium chloride; lithium hexamethyldisilazane; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; ethanol; dichloromethane; water; 1: Substitution / 2: Substitution / 3: hydroboration / 4: Elimination / 5: silylation / 6: Grignard reaction / 7: desilylation / 8: Oxidation;

DOI:10.1002/(SICI)1099-0690(199912)1999:12<3241::AID-EJOC3241>3.0.CO;2-9

Reference yield:

6,6-dimethyl-1,4-dioxaspiro[4.5]dec-7-en-7-yl trifluoromethanesulfonate (256469-23-5) → (5-cyclohex-2-enylmethyl-5-hydroxy-6,6-dimethyl-cyclohex-1-enyl)-acetaldehyde (256469-35-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 95 percent / LiCl; DBU / Pd(PPh₃)4 / tetrahydrofuran / 20 °C / Heating

2: 100 percent / 9-BBN; H₂O₂; NaOH / tetrahydrofuran; ethanol / 3 h / Heating

3: 99 percent / TsOH / tetrahydrofuran; H₂O / 18 h / Heating

4: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 15 h / 20 °C

5: 83 percent / Mg; CeCl₃ / tetrahydrofuran / 15 h / 0 - 20 °C

6: 71 percent / Bu₄NF / tetrahydrofuran / 15 h / 0 - 20 °C

7: 61 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -60 °C / 15 Torr

With dmap; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; cerium(III) chloride; oxalyl dichloride; tetrabutyl ammonium fluoride; dihydrogen peroxide; toluene-4-sulfonic acid; magnesium; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; ethanol; dichloromethane; water; 1: Substitution / 2: hydroboration / 3: Elimination / 4: silylation / 5: Grignard reaction / 6: desilylation / 7: Oxidation;

DOI:10.1002/(SICI)1099-0690(199912)1999:12<3241::AID-EJOC3241>3.0.CO;2-9

upstream raw materials:

1-cyclohex-2-enylmethyl-3-(2-hydroxy-ethyl)-2,2-dimethyl-cyclohex-3-enol

ethylene glycole monoacetal of 2,2-dimethylcyclohexane-1,3-dione

3-(2-hydroxyethyl)-2,2-dimethylcyclohex-3-en-1-one

2-(6,6-dimethyl-1,4-dioxa-spiro[4.5]dec-7-en-7-yl)-ethanol