(3-Methoxy-5-methyl-cyclohexa-2,5-dienyl)-methanol

Base Information

Chemical Name:(3-Methoxy-5-methyl-cyclohexa-2,5-dienyl)-methanol
CAS No.:142459-32-3
Molecular Formula:C₉H₁₄O₂
Molecular Weight:154.209
Hs Code.:

Synonyms:(3-Methoxy-5-methyl-cyclohexa-2,5-dienyl)-methanol

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Chemical Property of (3-Methoxy-5-methyl-cyclohexa-2,5-dienyl)-methanol

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Technology Process of (3-Methoxy-5-methyl-cyclohexa-2,5-dienyl)-methanol

There total 2 articles about (3-Methoxy-5-methyl-cyclohexa-2,5-dienyl)-methanol 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:

: 3-Methoxy-5-methyl-cyclohexa-2,5-dienecarboxylic acid methyl ester

: 142459-32-3
(3-Methoxy-5-methyl-cyclohexa-2,5-dienyl)-methanol

Guidance literature:: With diisobutylaluminium hydride; In diethyl ether; hexane; at -50 ℃; for 1.5h;
DOI:10.1021/jo00036a026

Reference yield:

: 124908-71-0
3-Methoxy-5-methyl-cyclohexa-2,5-dienecarboxylic acid

: 142459-32-3
(3-Methoxy-5-methyl-cyclohexa-2,5-dienyl)-methanol

Guidance literature:: Multi-step reaction with 2 steps

1: diethyl ether

2: 8.28 g / DIBALH / hexane; diethyl ether / 1.5 h / -50 °C

With diisobutylaluminium hydride; In diethyl ether; hexane;
DOI:10.1021/jo00036a026

Reference yield:

: 142459-32-3
(3-Methoxy-5-methyl-cyclohexa-2,5-dienyl)-methanol

: 142459-46-9
(R)-2-{(1R,2R,6S)-2-[(E)-3-Hydroxy-2-((2S,3S,6R)-6-{(E)-3-[(2S,5S)-5-((R)-1-methoxy-ethyl)-tetrahydro-furan-2-yl]-propenyl}-3-methyl-tetrahydro-pyran-2-yl)-propenyl]-6-methyl-cyclohexyl}-propionaldehyde

Guidance literature:: Multi-step reaction with 17 steps

1: 12.4 g / imidazole / CH₂Cl₂ / 0.25 h

2: 1) 2,6-di-tert-butylcresol, dichloromaleic anhydride 2) NaOMe / 1) chlorobenzene, 150 deg C, 24 h 2) MeOH, 0 deg C, 50 min

3: HF / acetonitrile / 1 h / 0 °C / Resolution: 1) isooctane, benzene, (Ac)2O, Amano lipase CES on Celite, 23 deg C, 5 h, 2) chromatography (silica gel, AcOEt/hexane), 3) recrystallization (Et₂O)

4: 99 percent / imidazole / CH₂Cl₂ / 1 h / Ambient temperature

5: 69 percent / 1) lithium hexamethyldisilazane, 2) HMPA / 1) THF, hexane, -50 deg C - -60 deg C, 1 h, 2) -35 deg C, 24 h

6: 98 percent / NH₂OH*HCl, pyridine / CH₂Cl₂ / 15 h / Heating

7: 1) TsCl, DMAP, pyridine, 2) LiCl, MeOH / 1) CH₂Cl₂, -80 deg C - r.t., 1 h, 2) r.t., 2 weeks

8: 72 percent / H₂ / 10percent Pd/C / ethanol

9: ethanol / 1.5 h / Heating

10: 627 mg / catecholborane, NaOAc*3H₂O / CHCl₃; tetrahydrofuran / 48 h / Heating

11: 473 mg / 5percent HF / acetonitrile / 0.75 h / 0 °C

12: 1) oxalyl chloride, DMSO, 2) Et₃N / 1) CH₂Cl₂, -80 deg C - -60 deg C, 1 h, 2) -60 deg C, 50 min

13: 1.23 g / LDA / tetrahydrofuran; hexane / 0.58 h / -100 °C

14: 1.17 g / DMAP, pyridine / 48 h / Ambient temperature

15: 1,8-diazabicyclo<5.4.0>undec-7-ene / 48 h / Ambient temperature

16: acetone / Irradiation

17: 50 mg / DIBALH / toluene; hexane / 0.58 h / -80 - -70 °C

With pyridine; 1H-imidazole; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; dichloromaleic acid anhydride; oxalyl dichloride; 2,4-di-t-butyl-3-methyl phenol; hydrogen fluoride; hydroxylamine hydrochloride; hydrogen; sodium methylate; sodium acetate; diisobutylaluminium hydride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; p-toluenesulfonyl chloride; lithium chloride; lithium hexamethyldisilazane; lithium diisopropyl amide; benzo[1,3,2]dioxaborole; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; chloroform; acetone; toluene; acetonitrile;
DOI:10.1021/jo00036a026