1,1,2-trimethyl-2-(2-methoxymethyloxy-5-methylphenyl)cyclopentane

Base Information

• Chemical Name: 1,1,2-trimethyl-2-(2-methoxymethyloxy-5-methylphenyl)cyclopentane
• CAS No.: 369610-41-3
• Molecular Formula: C₁₇H₂₆O₂
• Molecular Weight: 262.392
• Mol file: 369610-41-3.mol

Synonyms:1,1,2-trimethyl-2-(2-methoxymethyloxy-5-methylphenyl)cyclopentane

Chemical Property of 1,1,2-trimethyl-2-(2-methoxymethyloxy-5-methylphenyl)cyclopentane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,1,2-trimethyl-2-(2-methoxymethyloxy-5-methylphenyl)cyclopentane

There total 11 articles about 1,1,2-trimethyl-2-(2-methoxymethyloxy-5-methylphenyl)cyclopentane 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: 71.0%

4-methyl-2-[(1S)-1,2,2-trimethylcyclopentyl]phenol (81784-10-3) + chloromethyl methyl ether (107-30-2) → 1,1,2-trimethyl-2-(2-methoxymethyloxy-5-methylphenyl)cyclopentane (369610-41-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 23h;

DOI:10.1016/S0040-4020(01)00631-7

Reference yield:

N-(2-carbomethoxy-1-cyclopenten-1-yl)-(S)-valine tert-butyl ester (138200-47-2) → 1,1,2-trimethyl-2-(2-methoxymethyloxy-5-methylphenyl)cyclopentane (369610-41-3)

Guidance literature:

Multi-step reaction with 11 steps

1.1: LDA; HMPA / toluene; hexane / 0.5 h / -78 °C

1.2: toluene; hexane / 5 h / -25 °C

1.3: 40 percent / HCl / toluene; hexane; H₂O / 0.5 h / 0 °C

2.1: diethyl ether / 0.5 h / 20 °C

2.2: P₂O₅ / benzene / 2 h / 20 °C

2.3: 33 percent / KOH / methanol; H₂O / 72 h

3.1: Et₃N / tetrahydrofuran / 0.67 h / 20 °C

4.1: 416 mg / DMAP / benzene / 41 h / 20 °C

5.1: tri(o-tolyl)phosphine; n-Bu₃N / Pd(OAc)2 / dimethylformamide / 20 h / 120 °C

5.2: 58 mg / H₂ / Pd/C / ethanol / 18 h / 760 Torr

6.1: 56 mg / LiAlH₄ / tetrahydrofuran / 3 h / 20 °C

7.1: 98 percent / K₂CO₃ / acetone / 11 h / Heating

8.1: 96 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

9.1: 83 percent / NaOH; N₂H₄*H₂O / bis-(2-hydroxy-ethyl) ether / 150 - 180 °C

10.1: 66 percent / BBr₃ / CH₂Cl₂ / -78 - 20 °C

11.1: 71 percent / (i-Pr)2NEt / CH₂Cl₂ / 23 h / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; tributyl-amine; boron tribromide; potassium carbonate; hydrazine hydrate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; tris-(o-tolyl)phosphine; lithium diisopropyl amide; palladium diacetate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; diethylene glycol; benzene; 5.1: Intramolecular Heck reaction / 8.1: Swern oxidation / 9.1: Hunag-Minlon reaction;

DOI:10.1016/S0040-4020(01)00631-7

Reference yield:

methyl (R)-1-methyl-2-oxocyclopentanecarboxylate (162489-18-1) → 1,1,2-trimethyl-2-(2-methoxymethyloxy-5-methylphenyl)cyclopentane (369610-41-3)

Guidance literature:

Multi-step reaction with 10 steps

1.1: diethyl ether / 0.5 h / 20 °C

1.2: P₂O₅ / benzene / 2 h / 20 °C

1.3: 33 percent / KOH / methanol; H₂O / 72 h

2.1: Et₃N / tetrahydrofuran / 0.67 h / 20 °C

3.1: 416 mg / DMAP / benzene / 41 h / 20 °C

4.1: tri(o-tolyl)phosphine; n-Bu₃N / Pd(OAc)2 / dimethylformamide / 20 h / 120 °C

4.2: 58 mg / H₂ / Pd/C / ethanol / 18 h / 760 Torr

5.1: 56 mg / LiAlH₄ / tetrahydrofuran / 3 h / 20 °C

6.1: 98 percent / K₂CO₃ / acetone / 11 h / Heating

7.1: 96 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

8.1: 83 percent / NaOH; N₂H₄*H₂O / bis-(2-hydroxy-ethyl) ether / 150 - 180 °C

9.1: 66 percent / BBr₃ / CH₂Cl₂ / -78 - 20 °C

10.1: 71 percent / (i-Pr)2NEt / CH₂Cl₂ / 23 h / 20 °C

With dmap; sodium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; tributyl-amine; boron tribromide; potassium carbonate; hydrazine hydrate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; tris-(o-tolyl)phosphine; palladium diacetate; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; diethylene glycol; benzene; 4.1: Intramolecular Heck reaction / 7.1: Swern oxidation / 8.1: Hunag-Minlon reaction;

DOI:10.1016/S0040-4020(01)00631-7

upstream raw materials:

4-methyl-2-[(1S)-1,2,2-trimethylcyclopentyl]phenol

chloromethyl methyl ether

N-(2-carbomethoxy-1-cyclopenten-1-yl)-(S)-valine tert-butyl ester

(1S)-1,2,2-trimethyl-1-(2-methoxy-5-methyl)phenylcyclopentane

Downstream raw materials:

(-)-mastigophorene B

(S)-5-methyl-3-(1,2,2-trimethylcyclopentyl)benzene-1,2-diol

1,1,2-trimethyl-2-(3-hydroxy-2-methoxymethyloxy-5-methylphenyl)cyclopentane