(3R,3aR,6aR,10aR)-3-(2,6-Dimethoxy-4-methyl-phenyl)-4,7,7-trimethyl-3,3a,6,6a,7,8,9,10-octahydro-2-oxa-cyclopenta[d]naphthalene

Base Information

• Chemical Name: (3R,3aR,6aR,10aR)-3-(2,6-Dimethoxy-4-methyl-phenyl)-4,7,7-trimethyl-3,3a,6,6a,7,8,9,10-octahydro-2-oxa-cyclopenta[d]naphthalene
• CAS No.: 123502-41-0
• Molecular Formula: C₂₄H₃₄O₃
• Molecular Weight: 370.532
• Mol file: 123502-41-0.mol

Synonyms:

Chemical Property of (3R,3aR,6aR,10aR)-3-(2,6-Dimethoxy-4-methyl-phenyl)-4,7,7-trimethyl-3,3a,6,6a,7,8,9,10-octahydro-2-oxa-cyclopenta[d]naphthalene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,3aR,6aR,10aR)-3-(2,6-Dimethoxy-4-methyl-phenyl)-4,7,7-trimethyl-3,3a,6,6a,7,8,9,10-octahydro-2-oxa-cyclopenta[d]naphthalene

There total 12 articles about (3R,3aR,6aR,10aR)-3-(2,6-Dimethoxy-4-methyl-phenyl)-4,7,7-trimethyl-3,3a,6,6a,7,8,9,10-octahydro-2-oxa-cyclopenta[d]naphthalene 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:

(E)-3-methylpenta-2,4-dien-1-ol (1572-08-3) → (3R,3aR,6aR,10aR)-3-(2,6-Dimethoxy-4-methyl-phenyl)-4,7,7-trimethyl-3,3a,6,6a,7,8,9,10-octahydro-2-oxa-cyclopenta[d]naphthalene (123502-41-0)

Guidance literature:

Multi-step reaction with 12 steps

1: 83 percent / NaH / tetrahydrofuran / 8 h / Ambient temperature

2: 84 percent / FeCl₃ / diethyl ether / 48 h / -20 °C

3: tris(triphenylphosphine)rhodium(I) chloride / benzene

4: n-Bu₄NF / tetrahydrofuran

5: 72 percent / sodium bis(2-methoxyethoxy)aluminum hydride / diethyl ether; toluene / Ambient temperature

6: 72 percent / KH / 1,2-dimethoxy-ethane / -10 °C

7: NaH / 1,2-dimethoxy-ethane / Ambient temperature

8: tri-n-butyltin hydride, AIBN / toluene / Heating

9: Li, liquid NH₃, t-BuOH

10: pyridinium chlorochromate / CH₂Cl₂

11: 70 percent / diethyl ether / -78 - 20 °C

12: pyridinium chloride / CH₂Cl₂ / Heating

With 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; ammonia; tri-n-butyl-tin hydride; pyridine hydrochloride; lithium; potassium hydride; sodium hydride; sodium bis(2-methoxyethoxy)aluminium dihydride; pyridinium chlorochromate; tert-butyl alcohol; Wilkinson's catalyst; iron(III) chloride; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; dichloromethane; toluene; benzene;

DOI:10.1016/S0040-4039(00)82438-7

Reference yield:

(E)-3-methyl-5-benzyloxy-1,3-pentadiene (123502-30-7) → (3R,3aR,6aR,10aR)-3-(2,6-Dimethoxy-4-methyl-phenyl)-4,7,7-trimethyl-3,3a,6,6a,7,8,9,10-octahydro-2-oxa-cyclopenta[d]naphthalene (123502-41-0)

Guidance literature:

Multi-step reaction with 11 steps

1: 84 percent / FeCl₃ / diethyl ether / 48 h / -20 °C

2: tris(triphenylphosphine)rhodium(I) chloride / benzene

3: n-Bu₄NF / tetrahydrofuran

4: 72 percent / sodium bis(2-methoxyethoxy)aluminum hydride / diethyl ether; toluene / Ambient temperature

5: 72 percent / KH / 1,2-dimethoxy-ethane / -10 °C

6: NaH / 1,2-dimethoxy-ethane / Ambient temperature

7: tri-n-butyltin hydride, AIBN / toluene / Heating

8: Li, liquid NH₃, t-BuOH

9: pyridinium chlorochromate / CH₂Cl₂

10: 70 percent / diethyl ether / -78 - 20 °C

11: pyridinium chloride / CH₂Cl₂ / Heating

With 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; ammonia; tri-n-butyl-tin hydride; pyridine hydrochloride; lithium; potassium hydride; sodium hydride; sodium bis(2-methoxyethoxy)aluminium dihydride; pyridinium chlorochromate; tert-butyl alcohol; Wilkinson's catalyst; iron(III) chloride; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; dichloromethane; toluene; benzene;

DOI:10.1016/S0040-4039(00)82438-7

Reference yield:

(4aR,5R,8aR)-5-Benzyloxymethyl-1,1,6-trimethyl-4-oxo-1,5,8,8a-tetrahydro-4H-naphthalene-4a-carboxylic acid methyl ester (123502-31-8) → (3R,3aR,6aR,10aR)-3-(2,6-Dimethoxy-4-methyl-phenyl)-4,7,7-trimethyl-3,3a,6,6a,7,8,9,10-octahydro-2-oxa-cyclopenta[d]naphthalene (123502-41-0)

Guidance literature:

Multi-step reaction with 10 steps

1: tris(triphenylphosphine)rhodium(I) chloride / benzene

2: n-Bu₄NF / tetrahydrofuran

3: 72 percent / sodium bis(2-methoxyethoxy)aluminum hydride / diethyl ether; toluene / Ambient temperature

4: 72 percent / KH / 1,2-dimethoxy-ethane / -10 °C

5: NaH / 1,2-dimethoxy-ethane / Ambient temperature

6: tri-n-butyltin hydride, AIBN / toluene / Heating

7: Li, liquid NH₃, t-BuOH

8: pyridinium chlorochromate / CH₂Cl₂

9: 70 percent / diethyl ether / -78 - 20 °C

10: pyridinium chloride / CH₂Cl₂ / Heating

With 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; ammonia; tri-n-butyl-tin hydride; pyridine hydrochloride; lithium; potassium hydride; sodium hydride; sodium bis(2-methoxyethoxy)aluminium dihydride; pyridinium chlorochromate; tert-butyl alcohol; Wilkinson's catalyst; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; dichloromethane; toluene; benzene;

DOI:10.1016/S0040-4039(00)82438-7

upstream raw materials:

(2,6-Dimethoxy-4-methyl-phenyl)-((1S,4aS,8aS)-8a-methoxymethoxymethyl-2,5,5-trimethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-methanol

(E)-3-methylpenta-2,4-dien-1-ol

(E)-3-methyl-5-benzyloxy-1,3-pentadiene

((1R,4aR,8aR)-8a-Methoxymethoxymethyl-2,5,5-trimethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-methanol

Downstream raw materials:

3-Methoxy-5-methyl-2-((3R,3aR,6aR,10aR)-4,7,7-trimethyl-3,3a,6,6a,7,8,9,10-octahydro-2-oxa-cyclopenta[d]naphthalen-3-yl)-phenol