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

Base Information

• Chemical Name: 4-(5α-Methanesulfonyloxymethyl-2,6,6-trimethyl-2-cyclohexen-1α-yl)butanoic Acid
• CAS No.: 136179-85-6
• Molecular Formula: C₁₅H₂₆O₅S
• Molecular Weight: 318.434
• Mol file: 136179-85-6.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 17 articles about 4-(5α-Methanesulfonyloxymethyl-2,6,6-trimethyl-2-cyclohexen-1α-yl)butanoic Acid 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:

5-benzyloxy-1-pentanal (78999-24-3) → 4-(5α-Methanesulfonyloxymethyl-2,6,6-trimethyl-2-cyclohexen-1α-yl)butanoic Acid (136179-85-6)

Guidance literature:

Multi-step reaction with 15 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

12: pyridinium p-toluenesulfonate / CH₂Cl₂ / 1 h / Ambient temperature

13: 3.88 g / LiAlH₄ / diethyl ether / 0.17 h / 0 °C

14: 5.44 g / Et₃N / CH₂Cl₂ / 1 h / 0 °C

15: Jones reagent / acetone / 1 h / Ambient temperature

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

DOI:10.1248/cpb.39.1359

Reference yield:

5-(benzyloxy)-1-pentanol (4541-15-5) → 4-(5α-Methanesulfonyloxymethyl-2,6,6-trimethyl-2-cyclohexen-1α-yl)butanoic Acid (136179-85-6)

Guidance literature:

Multi-step reaction with 16 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

13: pyridinium p-toluenesulfonate / CH₂Cl₂ / 1 h / Ambient temperature

14: 3.88 g / LiAlH₄ / diethyl ether / 0.17 h / 0 °C

15: 5.44 g / Et₃N / CH₂Cl₂ / 1 h / 0 °C

16: Jones reagent / acetone / 1 h / Ambient temperature

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

DOI:10.1248/cpb.39.1359

Reference yield:

(E)-7-Benzyloxy-2-methyl-hept-2-en-1-ol (136180-01-3) → 4-(5α-Methanesulfonyloxymethyl-2,6,6-trimethyl-2-cyclohexen-1α-yl)butanoic Acid (136179-85-6)

Guidance literature:

Multi-step reaction with 13 steps

1: PCC / CH₂Cl₂

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

3: 82.6 percent / toluene / 17 h / 100 °C / bath temp.; hydroquinone for stabilization

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

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

6: 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

7: 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

8: 95.4 percent / pyridine / 2 h / Ambient temperature

9: 80 percent / Raney-Ni (W-2) / ethanol / 1 h / Heating

10: pyridinium p-toluenesulfonate / CH₂Cl₂ / 1 h / Ambient temperature

11: 3.88 g / LiAlH₄ / diethyl ether / 0.17 h / 0 °C

12: 5.44 g / Et₃N / CH₂Cl₂ / 1 h / 0 °C

13: Jones reagent / acetone / 1 h / Ambient temperature

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

DOI:10.1248/cpb.39.1359

upstream raw materials:

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

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

methanesulfonyl chloride

5-(benzyloxy)-1-pentanol

Downstream raw materials:

N-Methyl-2'-<(2-cyanoethyl)thio>-4-(5α-methanesulfonyloxymethyl-2,6,6-trimethyl-2-cyclohexen-1α-yl)butananilide