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

Base Information

• Chemical Name: Acetic acid (1S,4S)-4-bromomethyl-2,2-dimethyl-3-methylene-cyclohexylmethyl ester
• CAS No.: 73616-73-6
• Molecular Formula: C₁₃H₂₁BrO₂
• Molecular Weight: 289.213
• Mol file: 73616-73-6.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about Acetic acid (1S,4S)-4-bromomethyl-2,2-dimethyl-3-methylene-cyclohexylmethyl ester 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: 70.0%

Acetic acid (1S,4S)-4-hydroxymethyl-2,2-dimethyl-3-methylene-cyclohexylmethyl ester (80179-08-4) → Acetic acid (1S,4S)-4-bromomethyl-2,2-dimethyl-3-methylene-cyclohexylmethyl ester (73616-73-6,76231-57-7)

Guidance literature:

With carbon tetrabromide; triphenylphosphine; In diethyl ether; for 4h; Ambient temperature;

Reference yield: 63.0%

(+/-)-(1S,3S)-3-acetoxymethyl-1,2,2-trimethyl-1-vinylcyclopentane (73616-65-6) → Acetic acid (1S,4S)-4-bromomethyl-2,2-dimethyl-3-methylene-cyclohexylmethyl ester (73616-73-6,76231-57-7)

Guidance literature:

With 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one; In tetrahydrofuran; Heating;

DOI:10.1246/cl.1980.1001

Reference yield:

Acetic acid (1S,4S)-4-bromomethyl-2,2-dimethyl-3-methylene-cyclohexylmethyl ester (73616-73-6,76231-57-7) → 2-[(1R,5S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-5-methoxy-2,2,4-trimethyl-cyclohex-3-enyl]-ethanol (91318-88-6)

Guidance literature:

Multi-step reaction with 14 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: 3.65 mg / imidazole / dimethylformamide / 1 h / Ambient temperature

13: 50 percent NaH, sodium tertiary amylate / tetrahydrofuran / 0.25 h / Ambient temperature

14: 1) disiamylborane, water; 2) 3 N aq. NaOH, aq. 30 percent H₂O₂ / 1) THF, 30 min; 2) THF, 10 min

With 1H-imidazole; potassium hydroxide; sodium hydroxide; selenium(IV) oxide; ammonia; water; dihydrogen peroxide; sodium methylate; sodium; bis-(1,2-dimethylpropyl)borane; sodium tert-pentoxide; sodium hydride; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; silver(l) oxide; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1248/cpb.32.1294

upstream raw materials:

(+/-)-(1S,3S)-3-acetoxymethyl-1,2,2-trimethyl-1-vinylcyclopentane

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

Downstream raw materials:

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

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

(3S,6S)-3-Bromomethyl-6-(1-ethoxy-ethoxymethyl)-1,1-dimethyl-2-methylene-cyclohexane

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

Refernces

• 1、 Kitagawa, Isao,Shibuya, Hirotaka,Fujioka, Hiromichi,Kajiwara, Akiharu,Yamamoto, Yoshio,et al.. "CHEMICAL TRANSFORMATION OF TERPENOIDS. II. ACID TREATMENT OF (3S)-1-VINYL-,(3S)-1-HYDROXYPROPENYL-, AND (3S)-1-EPOXYETHYL-1,2,2-TRIMETHYLCYCLOPENTANE DERIVATIVES: RING ENLARGEMENT REACTIONS AND SUCCESSIVE MIGRATIONS OF METHYL RESIDUES". . p. 2548 - 2556. Retrieved 2007/10/02.