(4R,6S)-2-Chloromethyl-6-methoxy-4-(1-methoxy-1-methyl-ethoxymethyl)-1,3,3-trimethyl-cyclohexene

Base Information

• Chemical Name: (4R,6S)-2-Chloromethyl-6-methoxy-4-(1-methoxy-1-methyl-ethoxymethyl)-1,3,3-trimethyl-cyclohexene
• CAS No.: 81566-16-7
• Molecular Formula: C₁₆H₂₉ClO₃
• Molecular Weight: 304.857
• Mol file: 81566-16-7.mol

Synonyms:(4R,6S)-2-Chloromethyl-6-methoxy-4-(1-methoxy-1-methyl-ethoxymethyl)-1,3,3-trimethyl-cyclohexene

Chemical Property of (4R,6S)-2-Chloromethyl-6-methoxy-4-(1-methoxy-1-methyl-ethoxymethyl)-1,3,3-trimethyl-cyclohexene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,6S)-2-Chloromethyl-6-methoxy-4-(1-methoxy-1-methyl-ethoxymethyl)-1,3,3-trimethyl-cyclohexene

There total 20 articles about (4R,6S)-2-Chloromethyl-6-methoxy-4-(1-methoxy-1-methyl-ethoxymethyl)-1,3,3-trimethyl-cyclohexene 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:

Acetic acid (1S,4S)-4-bromomethyl-2,2-dimethyl-3-methylene-cyclohexylmethyl ester (73616-73-6,76231-57-7) → (4R,6S)-2-Chloromethyl-6-methoxy-4-(1-methoxy-1-methyl-ethoxymethyl)-1,3,3-trimethyl-cyclohexene (81566-16-7)

Guidance literature:

Multi-step reaction with 16 steps

1: 2.11 g / 10 percent KOH / methanol / 1.5 h / Ambient temperature

2: 97 percent / p-toluenesulfonic acid monohydrate / CH₂Cl₂ / 0.5 h

3: 42 percent / 80 percent m-chloroperbenzoic acid / CH₂Cl₂ / 1 h / Ambient temperature

4: 82 percent / sodium tertiary amylate / tetrahydrofuran; dimethylsulfoxide / 0.05 h / 70 °C

5: 92 percent / Na, liq. NH₃ / tetrahydrofuran / 0.5 h / -78 °C

6: 635 mg / pyridine / Ambient temperature

7: 92 percent / selenium dioxide / dioxane; pyridine / 2.5 h / 80 °C

8: 95 percent / silver oxide / dimethylformamide / 24 h / Ambient temperature

9: 96 percent / p-toluenesulfonic acid monohydrate / aq. ethanol / 1.5 h / Ambient temperature

10: 100 percent / pyridinium chlorochromate / CH₂Cl₂ / 2 h / Ambient temperature

11: 28 percent / 10 percent NaOMe / methanol / 0.5 h / Ambient temperature

12: 83 mg / pyridine / 2 h / Ambient temperature

13: 98 percent / sodium borohydride / methanol / 0.08 h

14: 184 mg / 1) phosphorus oxychloride; 2) Et₃N / 0.17 h / Ambient temperature

15: 160 mg / 2 N KOH / methanol / 0.5 h / Ambient temperature

16: 2,4,6-collidine, LiCl, mesyl chloride / 1,2-dimethoxy-ethane; dimethylformamide / 2.5 h

With 2,4,6-trimethyl-pyridine; potassium hydroxide; sodium tetrahydroborate; selenium(IV) oxide; ammonia; sodium methylate; sodium; sodium tert-pentoxide; toluene-4-sulfonic acid; methanesulfonyl chloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; lithium chloride; silver(l) oxide; trichlorophosphate; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1248/cpb.32.1294

Reference yield:

((1S,4S)-4-Bromomethyl-2,2-dimethyl-3-methylene-cyclohexyl)-methanol (91309-39-6) → (4R,6S)-2-Chloromethyl-6-methoxy-4-(1-methoxy-1-methyl-ethoxymethyl)-1,3,3-trimethyl-cyclohexene (81566-16-7)

Guidance literature:

Multi-step reaction with 15 steps

1: 97 percent / p-toluenesulfonic acid monohydrate / CH₂Cl₂ / 0.5 h

2: 42 percent / 80 percent m-chloroperbenzoic acid / CH₂Cl₂ / 1 h / Ambient temperature

3: 82 percent / sodium tertiary amylate / tetrahydrofuran; dimethylsulfoxide / 0.05 h / 70 °C

4: 92 percent / Na, liq. NH₃ / tetrahydrofuran / 0.5 h / -78 °C

5: 635 mg / pyridine / Ambient temperature

6: 92 percent / selenium dioxide / dioxane; pyridine / 2.5 h / 80 °C

7: 95 percent / silver oxide / dimethylformamide / 24 h / Ambient temperature

8: 96 percent / p-toluenesulfonic acid monohydrate / aq. ethanol / 1.5 h / Ambient temperature

9: 100 percent / pyridinium chlorochromate / CH₂Cl₂ / 2 h / Ambient temperature

10: 28 percent / 10 percent NaOMe / methanol / 0.5 h / Ambient temperature

11: 83 mg / pyridine / 2 h / Ambient temperature

12: 98 percent / sodium borohydride / methanol / 0.08 h

13: 184 mg / 1) phosphorus oxychloride; 2) Et₃N / 0.17 h / Ambient temperature

14: 160 mg / 2 N KOH / methanol / 0.5 h / Ambient temperature

15: 2,4,6-collidine, LiCl, mesyl chloride / 1,2-dimethoxy-ethane; dimethylformamide / 2.5 h

With 2,4,6-trimethyl-pyridine; potassium hydroxide; sodium tetrahydroborate; selenium(IV) oxide; ammonia; sodium methylate; sodium; sodium tert-pentoxide; toluene-4-sulfonic acid; methanesulfonyl chloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; lithium chloride; silver(l) oxide; trichlorophosphate; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1248/cpb.32.1294

Reference yield:

(3S,6S)-3-Bromomethyl-6-(2-ethoxy-ethoxymethyl)-1,1-dimethyl-2-methylene-cyclohexane → (4R,6S)-2-Chloromethyl-6-methoxy-4-(1-methoxy-1-methyl-ethoxymethyl)-1,3,3-trimethyl-cyclohexene (81566-16-7)

Guidance literature:

Multi-step reaction with 14 steps

1: 42 percent / 80 percent m-chloroperbenzoic acid / CH₂Cl₂ / 1 h / Ambient temperature

2: 82 percent / sodium tertiary amylate / tetrahydrofuran; dimethylsulfoxide / 0.05 h / 70 °C

3: 92 percent / Na, liq. NH₃ / tetrahydrofuran / 0.5 h / -78 °C

4: 635 mg / pyridine / Ambient temperature

5: 92 percent / selenium dioxide / dioxane; pyridine / 2.5 h / 80 °C

6: 95 percent / silver oxide / dimethylformamide / 24 h / Ambient temperature

7: 96 percent / p-toluenesulfonic acid monohydrate / aq. ethanol / 1.5 h / Ambient temperature

8: 100 percent / pyridinium chlorochromate / CH₂Cl₂ / 2 h / Ambient temperature

9: 28 percent / 10 percent NaOMe / methanol / 0.5 h / Ambient temperature

10: 83 mg / pyridine / 2 h / Ambient temperature

11: 98 percent / sodium borohydride / methanol / 0.08 h

12: 184 mg / 1) phosphorus oxychloride; 2) Et₃N / 0.17 h / Ambient temperature

13: 160 mg / 2 N KOH / methanol / 0.5 h / Ambient temperature

14: 2,4,6-collidine, LiCl, mesyl chloride / 1,2-dimethoxy-ethane; dimethylformamide / 2.5 h

With 2,4,6-trimethyl-pyridine; potassium hydroxide; sodium tetrahydroborate; selenium(IV) oxide; ammonia; sodium methylate; sodium; sodium tert-pentoxide; toluene-4-sulfonic acid; methanesulfonyl chloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; lithium chloride; silver(l) oxide; trichlorophosphate; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1248/cpb.32.1294

upstream raw materials:

[(3S,5R)-3-Methoxy-5-(1-methoxy-1-methyl-ethoxymethyl)-2,6,6-trimethyl-cyclohex-1-enyl]-methanol

Acetic acid (1S,4S)-4-bromomethyl-2,2-dimethyl-3-methylene-cyclohexylmethyl ester

((1S,4S)-4-Bromomethyl-2,2-dimethyl-3-methylene-cyclohexyl)-methanol

Acetic acid (3S,5R)-3-methoxy-5-(1-methoxy-1-methyl-ethoxymethyl)-2,6,6-trimethyl-cyclohex-1-enylmethyl ester

Downstream raw materials:

((1R,5S)-3-Chloromethyl-5-methoxy-2,2,4-trimethyl-cyclohex-3-enyl)-methanol