2-Cyclohexen-1-ol, 4-methyl-4-(1-propynyl)-, cis- (9CI)

Base Information

• Chemical Name: 2-Cyclohexen-1-ol, 4-methyl-4-(1-propynyl)-, cis- (9CI)
• CAS No.: 139599-54-5
• Molecular Formula: C10H14O
• Molecular Weight: 150.21756
• Mol file: 139599-54-5.mol

Synonyms:2-Cyclohexen-1-ol, 4-methyl-4-(1-propynyl)-, cis- (9CI)

Chemical Property of 2-Cyclohexen-1-ol, 4-methyl-4-(1-propynyl)-, cis- (9CI)

Chemical Property:

• PSA: 20.23000
• LogP: 1.72690

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Cyclohexen-1-ol, 4-methyl-4-(1-propynyl)-, cis- (9CI)

There total 9 articles about 2-Cyclohexen-1-ol, 4-methyl-4-(1-propynyl)-, cis- (9CI) 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:

(3S,6R)-6-(1-Ethoxy-ethoxy)-3-methyl-3-prop-1-ynyl-cyclohexene (139599-53-4) → 4β-methyl-4α-propynylcyclohex-2-en-1α-ol (139599-54-5)

Guidance literature:

With toluene-4-sulfonic acid; In ethanol; for 2h; Yield given;

Reference yield:

1-Methyl-cyclohexen-(2)-ol-(4)-carbonsaeure-aethylester (67394-30-3) → 4β-methyl-4α-propynylcyclohex-2-en-1α-ol (139599-54-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 94 percent / LiOH / tetrahydrofuran; H₂O

2: 90 percent / BF₃*Et₂O / CH₂Cl₂ / 3 h

3: 84 percent / diisobutylaluminium hydride (DIBAL) / CH₂Cl₂ / 0.5 h / -78 °C

4: 100 percent / p-toluenesulfonic acid / a) 0 deg C, 45 min, b) 0 deg C to RT, 2 h

5: 1.) NaN(SiMe₃)2 / 1.) THF, 2.) THF, a) -78 deg C, 5 min, b) from -78 deg C to RT, 1 h

6: NaN(SiMe₃)2 / tetrahydrofuran / 0.5 h

7: 1.) BuLi / 1.) THF, hexane, 0 deg C, 10 min, 2.) THF, hexane, 10 min

8: p-toluenesulfonic acid / ethanol / 2 h

With lithium hydroxide; n-butyllithium; boron trifluoride diethyl etherate; sodium hexamethyldisilazane; diisobutylaluminium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; ethanol; dichloromethane; water;

Reference yield:

1-methyl-4-oxo-cyclohex-2-enecarboxylic acid ethyl ester (1489-55-0) → 4β-methyl-4α-propynylcyclohex-2-en-1α-ol (139599-54-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) CeCl₃, 2.) NaBH₄ / 1.) MeOH, 30 min, 2.) MeOH

2: 94 percent / LiOH / tetrahydrofuran; H₂O

3: 90 percent / BF₃*Et₂O / CH₂Cl₂ / 3 h

4: 84 percent / diisobutylaluminium hydride (DIBAL) / CH₂Cl₂ / 0.5 h / -78 °C

5: 100 percent / p-toluenesulfonic acid / a) 0 deg C, 45 min, b) 0 deg C to RT, 2 h

6: 1.) NaN(SiMe₃)2 / 1.) THF, 2.) THF, a) -78 deg C, 5 min, b) from -78 deg C to RT, 1 h

7: NaN(SiMe₃)2 / tetrahydrofuran / 0.5 h

8: 1.) BuLi / 1.) THF, hexane, 0 deg C, 10 min, 2.) THF, hexane, 10 min

9: p-toluenesulfonic acid / ethanol / 2 h

With lithium hydroxide; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; boron trifluoride diethyl etherate; sodium hexamethyldisilazane; diisobutylaluminium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; ethanol; dichloromethane; water;

upstream raw materials:

(3S,6R)-6-(1-Ethoxy-ethoxy)-3-methyl-3-prop-1-ynyl-cyclohexene

1-Methyl-cyclohexen-⁽²⁾-ol-⁽⁴⁾-carbonsaeure-aethylester

1-methyl-4-oxo-cyclohex-2-enecarboxylic acid ethyl ester

4-methyl-2-oxabicyclo<2.2.2>oct-5-en-3-one

Downstream raw materials:

(3S,6R)-6-(1-Ethoxy-2-iodo-ethoxy)-3-methyl-3-prop-1-ynyl-cyclohexene

Refernces