4α-Acetoxymethyl-6α-(4-hydroxybutyl)-1,5,5-trimethylcyclohexene

Base Information

• Chemical Name: 4α-Acetoxymethyl-6α-(4-hydroxybutyl)-1,5,5-trimethylcyclohexene
• CAS No.: 136179-81-2
• Molecular Formula: C₁₆H₂₈O₃
• Molecular Weight: 268.397
• Mol file: 136179-81-2.mol

Synonyms:4α-Acetoxymethyl-6α-(4-hydroxybutyl)-1,5,5-trimethylcyclohexene

Chemical Property of 4α-Acetoxymethyl-6α-(4-hydroxybutyl)-1,5,5-trimethylcyclohexene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4α-Acetoxymethyl-6α-(4-hydroxybutyl)-1,5,5-trimethylcyclohexene

There total 13 articles about 4α-Acetoxymethyl-6α-(4-hydroxybutyl)-1,5,5-trimethylcyclohexene 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: 80.0%

6α-(4-Benzyloxybutyl)-4α-acetoxymethyl-1,5,5-trimethylcyclohexene (136179-79-8) → Acetic acid (1R,3S)-3-(4-hydroxy-butyl)-2,2,4-trimethyl-cyclohexylmethyl ester (136179-80-1) + 4α-Acetoxymethyl-6α-(4-hydroxybutyl)-1,5,5-trimethylcyclohexene (136179-81-2)

Guidance literature:

With Raney-Ni (W-2); In ethanol; for 1h; Heating;

DOI:10.1248/cpb.39.1359

Reference yield:

5-(benzyloxy)-1-pentanol (4541-15-5) → 4α-Acetoxymethyl-6α-(4-hydroxybutyl)-1,5,5-trimethylcyclohexene (136179-81-2)

Guidance literature:

Multi-step reaction with 12 steps

1: PCC / CH₂Cl₂ / 1.5 h / Ambient temperature

2: toluene / 10 h / 100 °C / bath temp.

3: LiAlH₄ / diethyl ether / 0.17 h / ice bath

4: PCC / CH₂Cl₂

5: 1.) BuLi / 1.) THF, hexane, -5 deg C to r.t., 30 min; 2.) -15 deg C to r.t., 30 min

6: 82.6 percent / toluene / 17 h / 100 °C / bath temp.; hydroquinone for stabilization

7: 1.) aq. NaHCO₃; 2.) NaHCO₃, I₂, KI / 1.) H₂O, boiling, 30 min; 2.) r.t., 3.5 h

8: 1.) BH₃*Me₂S; 2.) Zn powder / 1.) THF-B(OMe)3, r.t., 3 h; 2.) AcOH, reflux, 1 h

9: 1.) LDA, n-BuLi / 1.) THF, hexane, -15 deg C, 30 min; 2.) a) -78 deg C, 30 min, b) -15 deg C, 30 min

10: 1.) diisobutylaluminum hydride; 2.) NaOH, hydrazine hydrate / 1.) toluene, dry ice-acetone bath, 10 min; 2.) diethylene glycol, 110 to 210 deg C (bath temp.), 4 h

11: 95.4 percent / pyridine / 2 h / Ambient temperature

12: 80 percent / Raney-Ni (W-2) / ethanol / 1 h / Heating

With pyridine; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; dimethylsulfide borane complex; Raney-Ni (W-2); iodine; diisobutylaluminium hydride; sodium hydrogencarbonate; hydrazine hydrate; pyridinium chlorochromate; potassium iodide; zinc; lithium diisopropyl amide; In diethyl ether; ethanol; dichloromethane; toluene;

DOI:10.1248/cpb.39.1359

Reference yield:

5-benzyloxy-1-pentanal (78999-24-3) → 4α-Acetoxymethyl-6α-(4-hydroxybutyl)-1,5,5-trimethylcyclohexene (136179-81-2)

Guidance literature:

Multi-step reaction with 11 steps

1: toluene / 10 h / 100 °C / bath temp.

2: LiAlH₄ / diethyl ether / 0.17 h / ice bath

3: PCC / CH₂Cl₂

4: 1.) BuLi / 1.) THF, hexane, -5 deg C to r.t., 30 min; 2.) -15 deg C to r.t., 30 min

5: 82.6 percent / toluene / 17 h / 100 °C / bath temp.; hydroquinone for stabilization

6: 1.) aq. NaHCO₃; 2.) NaHCO₃, I₂, KI / 1.) H₂O, boiling, 30 min; 2.) r.t., 3.5 h

7: 1.) BH₃*Me₂S; 2.) Zn powder / 1.) THF-B(OMe)3, r.t., 3 h; 2.) AcOH, reflux, 1 h

8: 1.) LDA, n-BuLi / 1.) THF, hexane, -15 deg C, 30 min; 2.) a) -78 deg C, 30 min, b) -15 deg C, 30 min

9: 1.) diisobutylaluminum hydride; 2.) NaOH, hydrazine hydrate / 1.) toluene, dry ice-acetone bath, 10 min; 2.) diethylene glycol, 110 to 210 deg C (bath temp.), 4 h

10: 95.4 percent / pyridine / 2 h / Ambient temperature

11: 80 percent / Raney-Ni (W-2) / ethanol / 1 h / Heating

With pyridine; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; dimethylsulfide borane complex; Raney-Ni (W-2); iodine; diisobutylaluminium hydride; sodium hydrogencarbonate; hydrazine hydrate; pyridinium chlorochromate; potassium iodide; zinc; lithium diisopropyl amide; In diethyl ether; ethanol; dichloromethane; toluene;

DOI:10.1248/cpb.39.1359

upstream raw materials:

6α-(4-Benzyloxybutyl)-4α-acetoxymethyl-1,5,5-trimethylcyclohexene

5-(benzyloxy)-1-pentanol

5-benzyloxy-1-pentanal

(3E)-8-Benzyloxy-3-methyl-1,3-octadiene

Downstream raw materials:

4-(5α-Acetoxymethyl-2,6,6-trimethyl-2-cyclohexen-1α-yl)butanoic Acid

4-(5α-Hydroxymethyl-2,6,6-trimethyl-2-cyclohexen-1α-yl)butyl Tetrahydropyranyl Ether

4-(5α-Methanesulfonyloxymethyl-2,6,6-trimethyl-2-cyclohexen-1α-yl)butanoic Acid

4-(5α-Methanesulfonyloxymethyl-2,6,6-trimethyl-2-cyclohexen-1α-yl)butyl Tetrahydropyranyl Ether