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

Base Information

• Chemical Name: 3-Methoxy-5-methyl-cyclohexa-2,5-dienecarboxylic acid
• CAS No.: 124908-71-0
• Molecular Formula: C₉H₁₂O₃
• Molecular Weight: 168.192
• Mol file: 124908-71-0.mol

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

Chemical Property of 3-Methoxy-5-methyl-cyclohexa-2,5-dienecarboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-Methoxy-5-methyl-cyclohexa-2,5-dienecarboxylic acid

There total 1 articles about 3-Methoxy-5-methyl-cyclohexa-2,5-dienecarboxylic acid 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: 97.0%

3-methoxy-5-methylbenzoic acid (62089-34-3) → 3-Methoxy-5-methyl-cyclohexa-2,5-dienecarboxylic acid (124908-71-0)

Guidance literature:

With ammonia; sodium; In ethanol;

DOI:10.1039/c39890000712

Reference yield: 99.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + 3-Methoxy-5-methyl-cyclohexa-2,5-dienecarboxylic acid (124908-71-0) → 3-Methoxy-5-methyl-cyclohexa-2,5-dienecarboxylic acid methyl ester

Guidance literature:

In diethyl ether;

DOI:10.1039/c39890000712

Reference yield:

3-Methoxy-5-methyl-cyclohexa-2,5-dienecarboxylic acid (124908-71-0) → C41H68O8Si (142459-50-5)

Guidance literature:

Multi-step reaction with 21 steps

1: diethyl ether

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

3: 12.4 g / imidazole / CH₂Cl₂ / 0.25 h

4: 1) 2,6-di-tert-butylcresol, dichloromaleic anhydride 2) NaOMe / 1) chlorobenzene, 150 deg C, 24 h 2) MeOH, 0 deg C, 50 min

5: 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)

6: 99 percent / imidazole / CH₂Cl₂ / 1 h / Ambient temperature

7: 69 percent / 1) lithium hexamethyldisilazane, 2) HMPA / 1) THF, hexane, -50 deg C - -60 deg C, 1 h, 2) -35 deg C, 24 h

8: 98 percent / NH₂OH*HCl, pyridine / CH₂Cl₂ / 15 h / Heating

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

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

11: ethanol / 1.5 h / Heating

12: 627 mg / catecholborane, NaOAc*3H₂O / CHCl₃; tetrahydrofuran / 48 h / Heating

13: 473 mg / 5percent HF / acetonitrile / 0.75 h / 0 °C

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

15: 1.23 g / LDA / tetrahydrofuran; hexane / 0.58 h / -100 °C

16: 1.17 g / DMAP, pyridine / 48 h / Ambient temperature

17: 1,8-diazabicyclo<5.4.0>undec-7-ene / 48 h / Ambient temperature

18: acetone / Irradiation

19: 50 mg / DIBALH / toluene; hexane / 0.58 h / -80 - -70 °C

20: 44 mg / imidazole, Et₃N / CH₂Cl₂ / 0.58 h / Ambient temperature

21: 1) LDA, 2) N,N'-dimethylpropyleneurea / 1) THF, hexane, 2) THF, -100 deg C - -95 deg C, 20 min

With pyridine; 1H-imidazole; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 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; diethyl ether; ethanol; hexane; dichloromethane; chloroform; acetone; toluene; acetonitrile;

DOI:10.1021/jo00036a026

upstream raw materials:

3-methoxy-5-methylbenzoic acid

Downstream raw materials:

3-<<(tert-Butyldimethylsilyl)oxy>methyl>-1-methoxy-5-methyl-1,4-cyclohexadiene

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

(1R,2S,3S)-2-<(R)-1-Cyanoethyl>-1-(hydroxymethyl)-3-methylcyclohexane

(1R,2S,3S)-1-Formyl-2-<(1R)-1-cyanoethyl>-3-methylcyclohexane