(1S,2R,3S)-3-(2,2-dimethylpropoxy)-4,7,7-trimethylbicyclo<2.2.1>hept-2-yl (1R)-cyclohex-3-ene-1-carboxylate

Base Information

• Chemical Name: (1S,2R,3S)-3-(2,2-dimethylpropoxy)-4,7,7-trimethylbicyclo<2.2.1>hept-2-yl (1R)-cyclohex-3-ene-1-carboxylate
• CAS No.: 106618-24-0
• Molecular Formula: C₂₂H₃₆O₃
• Molecular Weight: 348.526
• Mol file: 106618-24-0.mol

Synonyms:(1S,2R,3S)-3-(2,2-dimethylpropoxy)-4,7,7-trimethylbicyclo<2.2.1>hept-2-yl (1R)-cyclohex-3-ene-1-carboxylate

Chemical Property of (1S,2R,3S)-3-(2,2-dimethylpropoxy)-4,7,7-trimethylbicyclo<2.2.1>hept-2-yl (1R)-cyclohex-3-ene-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,3S)-3-(2,2-dimethylpropoxy)-4,7,7-trimethylbicyclo<2.2.1>hept-2-yl (1R)-cyclohex-3-ene-1-carboxylate

There total 7 articles about (1S,2R,3S)-3-(2,2-dimethylpropoxy)-4,7,7-trimethylbicyclo<2.2.1>hept-2-yl (1R)-cyclohex-3-ene-1-carboxylate 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: 98.0%

(1S,2R,3S)-3-(2,2-dimethylpropoxy)-4,7,7-trimethylbicyclo<2.2.1>hept-2-yl acrylate (85696-02-2) + buta-1,3-diene (106-99-0,130983-70-9,29406-96-0,9003-17-2) → (1S,2R,3S)-3-(2,2-dimethylpropoxy)-4,7,7-trimethylbicyclo<2.2.1>hept-2-yl (1R)-cyclohex-3-ene-1-carboxylate (106618-24-0)

Guidance literature:

With titanium tetrachloride; In dichloromethane; at -8 ℃; for 112h;

DOI:10.1002/hlca.19850680803

Reference yield:

2,2-dimethylpropyl bromide (630-17-1) → (1S,2R,3S)-3-(2,2-dimethylpropoxy)-4,7,7-trimethylbicyclo<2.2.1>hept-2-yl (1R)-cyclohex-3-ene-1-carboxylate (106618-24-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 92.1 percent / 1.) NaH / 1.) N-methylpyrrolidone, 0 deg C, 1 h then r.t., 2 h; 2.) N-methylpyrrolidone, 100 deg C, 12 h then 130 deg C, 18 h

2: 96 percent / 50percent aq. H₂SO₄ / 24 h / 60 °C

3: 83.4 percent / NaBH₄ / methanol / 2 h / 0 °C

4: 91 percent / Et₃N / 4-(dimethylamino)pyridine / CH₂Cl₂ / 15 h / Ambient temperature

5: 98 percent / TiCl₄ / CH₂Cl₂ / 112 h / -8 °C

With sodium tetrahydroborate; sulfuric acid; titanium tetrachloride; sodium hydride; triethylamine; dmap; In methanol; dichloromethane;

DOI:10.1002/hlca.19850680803

Reference yield:

(1R,2S,3R,4S)-2-(2,2-dimethylpropoxy)-1,7,7-trimethylbicyclo<2.2.1>heptan-3-ol (85695-96-1) → (1S,2R,3S)-3-(2,2-dimethylpropoxy)-4,7,7-trimethylbicyclo<2.2.1>hept-2-yl (1R)-cyclohex-3-ene-1-carboxylate (106618-24-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / Et₃N / 4-(dimethylamino)pyridine / CH₂Cl₂ / 15 h / Ambient temperature

2: 98 percent / TiCl₄ / CH₂Cl₂ / 112 h / -8 °C

With titanium tetrachloride; triethylamine; dmap; In dichloromethane;

DOI:10.1002/hlca.19850680803

upstream raw materials:

(1S,2R,3S)-3-(2,2-dimethylpropoxy)-4,7,7-trimethylbicyclo<2.2.1>hept-2-yl acrylate

buta-1,3-diene

2,2-dimethylpropyl bromide

(1R,2S,3R,4S)-2-(2,2-dimethylpropoxy)-1,7,7-trimethylbicyclo<2.2.1>heptan-3-ol

Downstream raw materials:

(R)-1-C-(1-Cyclohexen-5-yl)methanol