(5-but-3-enyl-5-hydroxy-6,6-dimethyl-cyclohex-1-enyl)-acetaldehyde oxime

Base Information

Chemical Name:(5-but-3-enyl-5-hydroxy-6,6-dimethyl-cyclohex-1-enyl)-acetaldehyde oxime
CAS No.:256469-38-2
Molecular Formula:C₁₄H₂₃NO₂
Molecular Weight:237.342
Hs Code.:

Synonyms:(5-but-3-enyl-5-hydroxy-6,6-dimethyl-cyclohex-1-enyl)-acetaldehyde oxime

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Chemical Property of (5-but-3-enyl-5-hydroxy-6,6-dimethyl-cyclohex-1-enyl)-acetaldehyde oxime

Chemical Property:

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Technology Process of (5-but-3-enyl-5-hydroxy-6,6-dimethyl-cyclohex-1-enyl)-acetaldehyde oxime

There total 9 articles about (5-but-3-enyl-5-hydroxy-6,6-dimethyl-cyclohex-1-enyl)-acetaldehyde oxime 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: 99.0%

: 256469-36-0
(5-but-3-enyl-5-hydroxy-6,6-dimethyl-cyclohex-1-enyl)-acetaldehyde

: 256469-38-2
(5-but-3-enyl-5-hydroxy-6,6-dimethyl-cyclohex-1-enyl)-acetaldehyde oxime

Guidance literature:: With hydroxylamine hydrochloride; In dichloromethane; water; at 20 ℃; for 5h;
DOI:10.1002/(SICI)1099-0690(199912)1999:12<3241::AID-EJOC3241>3.0.CO;2-9

Reference yield:

: 14782-52-6
ethylene glycole monoacetal of 2,2-dimethylcyclohexane-1,3-dione

: 256469-38-2
(5-but-3-enyl-5-hydroxy-6,6-dimethyl-cyclohex-1-enyl)-acetaldehyde oxime

Guidance literature:: Multi-step reaction with 9 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: 90 percent / Mg; CeCl₃ / tetrahydrofuran / 15 h / 0 - 20 °C

7: 100 percent / Bu₄NF / tetrahydrofuran / 15 h / 0 - 20 °C

8: 89 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -60 °C / 15 Torr

9: 99 percent / NH₂OH*HCl / CH₂Cl₂; H₂O / 5 h / 20 °C

With dmap; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; cerium(III) chloride; oxalyl dichloride; hydroxylamine hydrochloride; 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 / 9: Condensation;
DOI:10.1002/(SICI)1099-0690(199912)1999:12<3241::AID-EJOC3241>3.0.CO;2-9

Reference yield:

: 256469-23-5
6,6-dimethyl-1,4-dioxaspiro[4.5]dec-7-en-7-yl trifluoromethanesulfonate

: 256469-38-2
(5-but-3-enyl-5-hydroxy-6,6-dimethyl-cyclohex-1-enyl)-acetaldehyde oxime

Guidance literature:: Multi-step reaction with 8 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: 90 percent / Mg; CeCl₃ / tetrahydrofuran / 15 h / 0 - 20 °C

6: 100 percent / Bu₄NF / tetrahydrofuran / 15 h / 0 - 20 °C

7: 89 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -60 °C / 15 Torr

8: 99 percent / NH₂OH*HCl / CH₂Cl₂; H₂O / 5 h / 20 °C

With dmap; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; cerium(III) chloride; oxalyl dichloride; hydroxylamine hydrochloride; 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 / 8: Condensation;
DOI:10.1002/(SICI)1099-0690(199912)1999:12<3241::AID-EJOC3241>3.0.CO;2-9