Acetic acid (1R,3S)-3-(4-hydroxy-butyl)-2,2,4-trimethyl-cyclohexylmethyl ester

Base Information

Chemical Name:Acetic acid (1R,3S)-3-(4-hydroxy-butyl)-2,2,4-trimethyl-cyclohexylmethyl ester
CAS No.:136179-80-1
Molecular Formula:C₁₆H₃₀O₃
Molecular Weight:270.412
Hs Code.:

Synonyms:Acetic acid (1R,3S)-3-(4-hydroxy-butyl)-2,2,4-trimethyl-cyclohexylmethyl ester

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Chemical Property of Acetic acid (1R,3S)-3-(4-hydroxy-butyl)-2,2,4-trimethyl-cyclohexylmethyl ester

Chemical Property:

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Technology Process of Acetic acid (1R,3S)-3-(4-hydroxy-butyl)-2,2,4-trimethyl-cyclohexylmethyl ester

There total 13 articles about Acetic acid (1R,3S)-3-(4-hydroxy-butyl)-2,2,4-trimethyl-cyclohexylmethyl ester 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%

: 136179-79-8
6α-(4-Benzyloxybutyl)-4α-acetoxymethyl-1,5,5-trimethylcyclohexene

: 136179-80-1
Acetic acid (1R,3S)-3-(4-hydroxy-butyl)-2,2,4-trimethyl-cyclohexylmethyl ester

: 136179-81-2
4α-Acetoxymethyl-6α-(4-hydroxybutyl)-1,5,5-trimethylcyclohexene

Guidance literature:: With Raney-Ni (W-2); In ethanol; for 1h; Heating;
DOI:10.1248/cpb.39.1359

Reference yield:

: 4541-15-5
5-(benzyloxy)-1-pentanol

: 136179-80-1
Acetic acid (1R,3S)-3-(4-hydroxy-butyl)-2,2,4-trimethyl-cyclohexylmethyl ester

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: hydrogen / Pd/C / ethanol

With pyridine; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; dimethylsulfide borane complex; hydrogen; iodine; diisobutylaluminium hydride; sodium hydrogencarbonate; hydrazine hydrate; pyridinium chlorochromate; potassium iodide; zinc; lithium diisopropyl amide; palladium on activated charcoal; In diethyl ether; ethanol; dichloromethane; toluene;
DOI:10.1248/cpb.39.1359

Reference yield:

: 78999-24-3
5-benzyloxy-1-pentanal

: 136179-80-1
Acetic acid (1R,3S)-3-(4-hydroxy-butyl)-2,2,4-trimethyl-cyclohexylmethyl ester

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: hydrogen / Pd/C / ethanol

With pyridine; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; dimethylsulfide borane complex; hydrogen; iodine; diisobutylaluminium hydride; sodium hydrogencarbonate; hydrazine hydrate; pyridinium chlorochromate; potassium iodide; zinc; lithium diisopropyl amide; palladium on activated charcoal; In diethyl ether; ethanol; dichloromethane; toluene;
DOI:10.1248/cpb.39.1359