(3R,4S)-3-(2-hydroxyethyl)-4-isopropenyl-3-methylcyclohexanone

Base Information

• Chemical Name: (3R,4S)-3-(2-hydroxyethyl)-4-isopropenyl-3-methylcyclohexanone
• CAS No.: 144264-23-3
• Molecular Formula: C₁₂H₂₀O₂
• Molecular Weight: 196.29
• Mol file: 144264-23-3.mol

Synonyms:(3R,4S)-3-(2-hydroxyethyl)-4-isopropenyl-3-methylcyclohexanone

Chemical Property of (3R,4S)-3-(2-hydroxyethyl)-4-isopropenyl-3-methylcyclohexanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S)-3-(2-hydroxyethyl)-4-isopropenyl-3-methylcyclohexanone

There total 6 articles about (3R,4S)-3-(2-hydroxyethyl)-4-isopropenyl-3-methylcyclohexanone 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: 93.0%

(4S,5R)-1-acetoxy-5-(2-acetoxyethyl)-4-isopropenyl-5-methyl-1-cyclohexene (144264-22-2) → (3R,4S)-3-(2-hydroxyethyl)-4-isopropenyl-3-methylcyclohexanone (144264-23-3)

Guidance literature:

With potassium carbonate; In methanol; a) 0 deg C, 1 h, b) RT, 1 h;

DOI:10.1246/bcsj.65.2071

Reference yield:

(1R,4S,5R)-(+)-4,6,6-trimethyl-4-vinylbicyclo<3.1.1>heptan-2-one (128261-62-1) → (3R,4S)-3-(2-hydroxyethyl)-4-isopropenyl-3-methylcyclohexanone (144264-23-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 85 percent / p-toluenesulfonic acid / benzene / 13 h

2: 1.) 9-borabicyclo<3.3.1>nonane (9-BBN), 2.) aq. NaOH, 30percent H₂O₂ / 1.) THF, a) 0 deg C, 30 min, b) RT, 17 h, 2.) THF, a) 0 deg C, 30 min, b) RT, 6 h

3: 96 percent / pyridine / 10 h / Ambient temperature

4: 93 percent / p-toluenesulfonic acid / acetone / 4 h / Ambient temperature

5: 79 percent / BF₃*Et₂O, (CH₃COO)2Zn / 96 h / Ambient temperature

6: 93 percent / K₂CO₃ / methanol / a) 0 deg C, 1 h, b) RT, 1 h

With pyridine; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; boron trifluoride diethyl etherate; zinc diacetate; dihydrogen peroxide; potassium carbonate; toluene-4-sulfonic acid; In methanol; acetone; benzene;

DOI:10.1246/bcsj.65.2071

Reference yield:

(1R,4S,5R)-4,6,6-trimethyl-4-vinylbicyclo<3.1.1>heptan-2-one ethylene acetal (144264-18-6) → (3R,4S)-3-(2-hydroxyethyl)-4-isopropenyl-3-methylcyclohexanone (144264-23-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) 9-borabicyclo<3.3.1>nonane (9-BBN), 2.) aq. NaOH, 30percent H₂O₂ / 1.) THF, a) 0 deg C, 30 min, b) RT, 17 h, 2.) THF, a) 0 deg C, 30 min, b) RT, 6 h

2: 96 percent / pyridine / 10 h / Ambient temperature

3: 93 percent / p-toluenesulfonic acid / acetone / 4 h / Ambient temperature

4: 79 percent / BF₃*Et₂O, (CH₃COO)2Zn / 96 h / Ambient temperature

5: 93 percent / K₂CO₃ / methanol / a) 0 deg C, 1 h, b) RT, 1 h

With pyridine; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; boron trifluoride diethyl etherate; zinc diacetate; dihydrogen peroxide; potassium carbonate; toluene-4-sulfonic acid; In methanol; acetone;

DOI:10.1246/bcsj.65.2071

upstream raw materials:

(4S,5R)-1-acetoxy-5-(2-acetoxyethyl)-4-isopropenyl-5-methyl-1-cyclohexene

(1R,4S,5R)-(+)-4,6,6-trimethyl-4-vinylbicyclo<3.1.1>heptan-2-one

(1R,4R,5R)-4-(2-hydroxyethyl)-4,6,6-trimethylbicyclo<3.1.1>heptan-2-one ethylene acetal

(1R,4S,5R)-4,6,6-trimethyl-4-vinylbicyclo<3.1.1>heptan-2-one ethylene acetal

Downstream raw materials:

(3R,4S)-3-(2-acetoxyethyl)-4-isopropenyl-3-methylcyclohexanone