Acetic acid 2-[(1R,5S)-5-(2-chlorocarbonyl-ethyl)-2,6,6-trimethyl-cyclohex-2-enyl]-ethyl ester

Base Information

Chemical Name:Acetic acid 2-[(1R,5S)-5-(2-chlorocarbonyl-ethyl)-2,6,6-trimethyl-cyclohex-2-enyl]-ethyl ester
CAS No.:123887-21-8
Molecular Formula:C₁₆H₂₅ClO₃
Molecular Weight:300.826
Hs Code.:

Synonyms:

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Chemical Property of Acetic acid 2-[(1R,5S)-5-(2-chlorocarbonyl-ethyl)-2,6,6-trimethyl-cyclohex-2-enyl]-ethyl ester

Chemical Property:

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Technology Process of Acetic acid 2-[(1R,5S)-5-(2-chlorocarbonyl-ethyl)-2,6,6-trimethyl-cyclohex-2-enyl]-ethyl ester

There total 13 articles about Acetic acid 2-[(1R,5S)-5-(2-chlorocarbonyl-ethyl)-2,6,6-trimethyl-cyclohex-2-enyl]-ethyl 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:

: 123886-96-4
3-[(1S,3R,4S,5R)-5-Benzyloxycarbonyloxy-2,2,4-trimethyl-3-(3-oxo-butyl)-cyclohexyl]-propionic acid ethyl ester

: 123887-21-8
Acetic acid 2-[(1R,5S)-5-(2-chlorocarbonyl-ethyl)-2,6,6-trimethyl-cyclohex-2-enyl]-ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 82.6 percent / mCPBA / 1,2-dichloro-ethane / 44 h / 55 °C

2: 89.5 percent / hydrogen / 10percent Pd-C / ethanol / 0.5 h / Ambient temperature

3: 89.1 percent / diethyl azodicarboxylate, triphenylphosphine / tetrahydrofuran / 12 h / Ambient temperature

4: 400 mg / 1.) KOH; 2.) Ac₂O / Ambient temperature; 1.) aq. EtOH; 2.) pyridine

5: oxalyl chloride / benzene / 1 h, rt. then 1 h, 60 deg C

With potassium hydroxide; oxalyl dichloride; hydrogen; acetic anhydride; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; ethanol; 1,2-dichloro-ethane; benzene;
DOI:10.1248/cpb.36.4722

Reference yield:

: 123886-93-1
ethyl 3-(5α-hydroxy-2,2,4α-trimethyl-3α-(3-oxobutyl)cyclohexan-1α-yl)propionate

: 123887-21-8
Acetic acid 2-[(1R,5S)-5-(2-chlorocarbonyl-ethyl)-2,6,6-trimethyl-cyclohex-2-enyl]-ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 24.8 percent / mCPBA / 1,2-dichloro-ethane / 60 h / 55 °C

2: 89.1 percent / diethyl azodicarboxylate, triphenylphosphine / tetrahydrofuran / 12 h / Ambient temperature

3: 400 mg / 1.) KOH; 2.) Ac₂O / Ambient temperature; 1.) aq. EtOH; 2.) pyridine

4: oxalyl chloride / benzene / 1 h, rt. then 1 h, 60 deg C

With potassium hydroxide; oxalyl dichloride; acetic anhydride; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1,2-dichloro-ethane; benzene;
DOI:10.1248/cpb.36.4722

Reference yield:

: 123886-91-9
{(1S,3R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2,2,4-trimethyl-3-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-cyclohexyl}-methanol

: 123887-21-8
Acetic acid 2-[(1R,5S)-5-(2-chlorocarbonyl-ethyl)-2,6,6-trimethyl-cyclohex-2-enyl]-ethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 1.35 g / AcONa*3H₂O, PCC / CH₂Cl₂ / 2.5 h / Ambient temperature

2: toluene / 16 h / 100 °C

3: 851 mg / PtO₂/hydrogen / ethyl acetate / 0.5 h / Ambient temperature

4: 1.) p-toluenesulfonic acid / 1.) acetone, rt., 5 h; 2.) EtOH, 50 deg C, 5 h

5: 24.8 percent / mCPBA / 1,2-dichloro-ethane / 60 h / 55 °C

6: 89.1 percent / diethyl azodicarboxylate, triphenylphosphine / tetrahydrofuran / 12 h / Ambient temperature

7: 400 mg / 1.) KOH; 2.) Ac₂O / Ambient temperature; 1.) aq. EtOH; 2.) pyridine

8: oxalyl chloride / benzene / 1 h, rt. then 1 h, 60 deg C

With platinum(IV) oxide; potassium hydroxide; oxalyl dichloride; hydrogen; sodium acetate; acetic anhydride; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; pyridinium chlorochromate; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; ethyl acetate; 1,2-dichloro-ethane; toluene; benzene;
DOI:10.1248/cpb.36.4722