(-)-(1R,5S)-2,5,6,6-tetramethylcyclohex-2-ene-1-carbaldehyde

Base Information

Chemical Name:(-)-(1R,5S)-2,5,6,6-tetramethylcyclohex-2-ene-1-carbaldehyde
CAS No.:124988-45-0
Molecular Formula:C₁₁H₁₈O
Molecular Weight:166.263
Hs Code.:

Synonyms:

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Chemical Property of (-)-(1R,5S)-2,5,6,6-tetramethylcyclohex-2-ene-1-carbaldehyde

Chemical Property:

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Technology Process of (-)-(1R,5S)-2,5,6,6-tetramethylcyclohex-2-ene-1-carbaldehyde

There total 12 articles about (-)-(1R,5S)-2,5,6,6-tetramethylcyclohex-2-ene-1-carbaldehyde 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:

: 153060-96-9
(+)-(1R,5S)-2,5,6,6-tetramethylcyclohex-2-ene-1-methanol

: 124988-45-0
(-)-(1R,5S)-2,5,6,6-tetramethylcyclohex-2-ene-1-carbaldehyde

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; Yield given. Multistep reaction; 1.) CH₂Cl₂, -70 deg, 15 min; 2.) CH₂Cl₂, room temp., 30 min;
DOI:10.1002/hlca.19930760521

Reference yield:

: 140632-38-8
(+)-(3R,7S)-4,7,8,8-tetramethyl-1-oxaspiro<2.5>oct-4-ene

: 124988-45-0
(-)-(1R,5S)-2,5,6,6-tetramethylcyclohex-2-ene-1-carbaldehyde

: 153060-94-7
(+)-(1S,5S)-2,5,6,6-tetramethylcyclohex-2-ene-1-carbaldehyde

Guidance literature:: With tin(IV) chloride; In toluene; at 0 ℃; Yield given;
DOI:10.1002/hlca.19930760521

Reference yield:

: 815581-75-0
(1S,5R)-5-(hydroxymethyl)-4,6,6-trimethylcyclohex-3-enol

: 124988-45-0
(-)-(1R,5S)-2,5,6,6-tetramethylcyclohex-2-ene-1-carbaldehyde

Guidance literature:: Multi-step reaction with 10 steps

1.1: 1H-imidazole; dmap / dichloromethane / 2 h / 20 °C

2.1: 4-methylmorpholine N-oxide / dichloromethane / 0.17 h / 20 °C / Molecular sieve

2.2: 3 h / 20 °C

3.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / 20 °C

3.2: 20 h / 20 - 70 °C

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 16 h / 20 °C

5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / 0 °C

6.1: 1H-imidazole; dmap / dichloromethane / 2 h / 20 °C

7.1: hydrogen; palladium 10% on activated carbon / ethyl acetate / 24 h / 22 °C

8.1: acetic acid; zinc; sodium acetate; sodium iodide / dichloromethane / 24 h / 20 - 40 °C

9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 22 °C

10.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 2 h / 20 °C

With 1H-imidazole; dmap; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; sodium acetate; sodium hexamethyldisilazane; acetic acid; 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid; sodium iodide; zinc; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; ethyl acetate; 3.1: |Wittig Olefination / 3.2: |Wittig Olefination;
DOI:10.1002/chem.201404642