benzyl (1'R,2'R)-3-(6',6'-ethylenedioxy-1',2'-dimethyl-3'-oxocyclohexane)propanoate

Base Information Edit

Chemical Name:benzyl (1'R,2'R)-3-(6',6'-ethylenedioxy-1',2'-dimethyl-3'-oxocyclohexane)propanoate
CAS No.:122052-63-5
Molecular Formula:C₂₀H₂₆O₅
Molecular Weight:346.423
Hs Code.:
Mol file:122052-63-5.mol

Synonyms:

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Chemical Property of benzyl (1'R,2'R)-3-(6',6'-ethylenedioxy-1',2'-dimethyl-3'-oxocyclohexane)propanoate Edit

Chemical Property:

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Technology Process of benzyl (1'R,2'R)-3-(6',6'-ethylenedioxy-1',2'-dimethyl-3'-oxocyclohexane)propanoate

There total 17 articles about benzyl (1'R,2'R)-3-(6',6'-ethylenedioxy-1',2'-dimethyl-3'-oxocyclohexane)propanoate 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:

: 14160-65-7,77793-24-9,122090-88-4
ethyl 8-oxo-1,4-dioxaspiro[4.5]decane-7-carboxylate

: 122052-63-5
benzyl (1'R,2'R)-3-(6',6'-ethylenedioxy-1',2'-dimethyl-3'-oxocyclohexane)propanoate

Guidance literature:: Multi-step reaction with 16 steps

1: 10 g / baker's yeast, sucrose / H₂O; ethanol / 30 °C

2: 4-N,N-dimethylaminopyridine / pyridine / Ambient temperature

3: 95 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

4: 87 percent / p-TsOH / CH₂Cl₂ / 3 h / Ambient temperature

5: 83 percent / NBS / AIBN / benzene / 1 h / 50 °C

6: 83 percent / LiAlH₄ / tetrahydrofuran / Ambient temperature

7: 99 percent / Amberlite IR-120 / H₂O / 3 h / Heating

8: 90 percent / p-TsOH / CH₂Cl₂ / Ambient temperature

9: 60percent NaH / tetrahydrofuran / 1 h / Ambient temperature

10: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / 0 °C

11: 1.) p-TsCl / 1.) pyridine, 0 deg C, 3 h, 2.) pyridine, room temp.

12: t-BuOK / 2-methyl-propan-2-ol / 2 h / Ambient temperature

13: 25percent aq. KOH / bis-(2-hydroxy-ethyl) ether / 24 h / Heating

14: 2.) LiOH*H₂O / 1.) p-TsOH / 1.) benzene, 6 h, reflux, 2.) H₂O, MeOH, room temp.

15: NaHCO₃ / dimethylformamide / 60 °C

16: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -70 deg C, 1.5 h, 2.) CH₂Cl₂, -70 -> 0 deg C

With potassium hydroxide; lithium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; baker's yeast; oxalyl dichloride; Amberlite IR-120; potassium tert-butylate; sodium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; p-toluenesulfonyl chloride; lithium diisopropyl amide; Sucrose; dmap; 2,2'-azobis(isobutyronitrile); toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; diethylene glycol; benzene;
DOI:10.1016/S0040-4020(01)86136-6

Reference yield:

: 96893-99-1
(1R,2S)-5,5-(Ethylendioxy)-2-hydroxycyclohexancarbonsaeure-ethylester

: 122052-63-5
benzyl (1'R,2'R)-3-(6',6'-ethylenedioxy-1',2'-dimethyl-3'-oxocyclohexane)propanoate

Guidance literature:: Multi-step reaction with 15 steps

1: 4-N,N-dimethylaminopyridine / pyridine / Ambient temperature

2: 95 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

3: 87 percent / p-TsOH / CH₂Cl₂ / 3 h / Ambient temperature

4: 83 percent / NBS / AIBN / benzene / 1 h / 50 °C

5: 83 percent / LiAlH₄ / tetrahydrofuran / Ambient temperature

6: 99 percent / Amberlite IR-120 / H₂O / 3 h / Heating

7: 90 percent / p-TsOH / CH₂Cl₂ / Ambient temperature

8: 60percent NaH / tetrahydrofuran / 1 h / Ambient temperature

9: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / 0 °C

10: 1.) p-TsCl / 1.) pyridine, 0 deg C, 3 h, 2.) pyridine, room temp.

11: t-BuOK / 2-methyl-propan-2-ol / 2 h / Ambient temperature

12: 25percent aq. KOH / bis-(2-hydroxy-ethyl) ether / 24 h / Heating

13: 2.) LiOH*H₂O / 1.) p-TsOH / 1.) benzene, 6 h, reflux, 2.) H₂O, MeOH, room temp.

14: NaHCO₃ / dimethylformamide / 60 °C

15: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -70 deg C, 1.5 h, 2.) CH₂Cl₂, -70 -> 0 deg C

With potassium hydroxide; lithium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; oxalyl dichloride; Amberlite IR-120; potassium tert-butylate; sodium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; p-toluenesulfonyl chloride; lithium diisopropyl amide; dmap; 2,2'-azobis(isobutyronitrile); toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; diethylene glycol; benzene;
DOI:10.1016/S0040-4020(01)86136-6

Reference yield:

: 96894-00-7
(1S,2S)-4,4-ethylenedioxy-2-hydroxymethylcyclohexanol

: 122052-63-5
benzyl (1'R,2'R)-3-(6',6'-ethylenedioxy-1',2'-dimethyl-3'-oxocyclohexane)propanoate

Guidance literature:: Multi-step reaction with 13 steps

1: 87 percent / p-TsOH / CH₂Cl₂ / 3 h / Ambient temperature

2: 83 percent / NBS / AIBN / benzene / 1 h / 50 °C

3: 83 percent / LiAlH₄ / tetrahydrofuran / Ambient temperature

4: 99 percent / Amberlite IR-120 / H₂O / 3 h / Heating

5: 90 percent / p-TsOH / CH₂Cl₂ / Ambient temperature

6: 60percent NaH / tetrahydrofuran / 1 h / Ambient temperature

7: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / 0 °C

8: 1.) p-TsCl / 1.) pyridine, 0 deg C, 3 h, 2.) pyridine, room temp.

9: t-BuOK / 2-methyl-propan-2-ol / 2 h / Ambient temperature

10: 25percent aq. KOH / bis-(2-hydroxy-ethyl) ether / 24 h / Heating

11: 2.) LiOH*H₂O / 1.) p-TsOH / 1.) benzene, 6 h, reflux, 2.) H₂O, MeOH, room temp.

12: NaHCO₃ / dimethylformamide / 60 °C

13: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -70 deg C, 1.5 h, 2.) CH₂Cl₂, -70 -> 0 deg C

With potassium hydroxide; lithium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; oxalyl dichloride; Amberlite IR-120; potassium tert-butylate; sodium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; p-toluenesulfonyl chloride; lithium diisopropyl amide; 2,2'-azobis(isobutyronitrile); toluene-4-sulfonic acid; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; diethylene glycol; benzene;
DOI:10.1016/S0040-4020(01)86136-6