4-hydroxy-1,1-cyclohexanedicarboxylic acid-1,1-bis(tert-butyl)ester

Base Information

Chemical Name:4-hydroxy-1,1-cyclohexanedicarboxylic acid-1,1-bis(tert-butyl)ester
CAS No.:1318651-93-2
Molecular Formula:C₁₆H₂₈O₅
Molecular Weight:300.395
Hs Code.:

Synonyms:4-hydroxy-1,1-cyclohexanedicarboxylic acid-1,1-bis(tert-butyl)ester

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Chemical Property of 4-hydroxy-1,1-cyclohexanedicarboxylic acid-1,1-bis(tert-butyl)ester

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Technology Process of 4-hydroxy-1,1-cyclohexanedicarboxylic acid-1,1-bis(tert-butyl)ester

There total 1 articles about 4-hydroxy-1,1-cyclohexanedicarboxylic acid-1,1-bis(tert-butyl)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: 99.0%

: 925704-44-5
4-oxo-1,1-cyclohexanedicarboxylic acid 1,1-bis(tert-butyl)ester

: 1318651-93-2
4-hydroxy-1,1-cyclohexanedicarboxylic acid-1,1-bis(tert-butyl)ester

Guidance literature:: With sodium tetrahydroborate; In ethanol; at 0 ℃; for 0.5h;
DOI:10.1021/ol2018533

Reference yield:

: 1318651-93-2
4-hydroxy-1,1-cyclohexanedicarboxylic acid-1,1-bis(tert-butyl)ester

: 4-(4-methoxybenzyl)spiro[4.5]dec-1-en-8-ol

Guidance literature:: Multi-step reaction with 15 steps

1.1: toluene-4-sulfonic acid / benzene / 3 h / Reflux

2.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 2 h / 20 °C

3.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 2 h / Reflux; Inert atmosphere

4.1: chloro-trimethyl-silane; water / acetonitrile / 0.5 h / 20 °C

5.1: cerium(III) chloride heptahydrate / ethanol; dichloromethane / 2 h / 20 °C

5.2: 2 h / 0 °C

6.1: sodium iodide / acetone / 14 h / Reflux

7.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

8.1: nickel(II) iodide; samarium diiodide / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

9.1: N-ethyl-N,N-diisopropylamine; sodium iodide / dichloromethane / 0 - 20 °C

10.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

10.2: 1 h / -78 °C / Inert atmosphere

11.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 0.5 h / Reflux

12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C

13.1: Crabtree's catalyst; hydrogen / dichloromethane / 1 h / 20 °C

14.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 13 h / 20 °C / Inert atmosphere

15.1: hydrogenchloride / methanol / 17 h / 20 °C

With 2,6-dimethylpyridine; nickel(II) iodide; hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; chloro-trimethyl-silane; samarium diiodide; oxalyl dichloride; Crabtree's catalyst; cerium(III) chloride heptahydrate; tetrabutyl ammonium fluoride; water; hydrogen; sodium hexamethyldisilazane; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; triphenylphosphine; sodium iodide; diethylazodicarboxylate; In tetrahydrofuran; methanol; ethanol; dichloromethane; acetone; acetonitrile; benzene; 8.1: Barbier reaction / 14.1: Mitsunobu reaction;
DOI:10.1021/ol2018533

Reference yield:

: 1318651-93-2
4-hydroxy-1,1-cyclohexanedicarboxylic acid-1,1-bis(tert-butyl)ester

: 4-(4-hydroxybenzyl)spiro[4.5]dec-1-en-8-ol

Guidance literature:: Multi-step reaction with 16 steps

1.1: toluene-4-sulfonic acid / benzene / 3 h / Reflux

2.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 2 h / 20 °C

3.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 2 h / Reflux; Inert atmosphere

4.1: chloro-trimethyl-silane; water / acetonitrile / 0.5 h / 20 °C

5.1: cerium(III) chloride heptahydrate / ethanol; dichloromethane / 2 h / 20 °C

5.2: 2 h / 0 °C

6.1: sodium iodide / acetone / 14 h / Reflux

7.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

8.1: nickel(II) iodide; samarium diiodide / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

9.1: N-ethyl-N,N-diisopropylamine; sodium iodide / dichloromethane / 0 - 20 °C

10.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

10.2: 1 h / -78 °C / Inert atmosphere

11.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 0.5 h / Reflux

12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C

13.1: Crabtree's catalyst; hydrogen / dichloromethane / 1 h / 20 °C

14.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 13 h / 20 °C / Inert atmosphere

15.1: hydrogenchloride / methanol / 17 h / 20 °C

16.1: potassium tert-butylate; 1-dodecylthiol / N,N-dimethyl-formamide / 3 h / Reflux

With 2,6-dimethylpyridine; nickel(II) iodide; hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; chloro-trimethyl-silane; samarium diiodide; oxalyl dichloride; Crabtree's catalyst; cerium(III) chloride heptahydrate; potassium tert-butylate; tetrabutyl ammonium fluoride; water; hydrogen; sodium hexamethyldisilazane; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; triphenylphosphine; sodium iodide; diethylazodicarboxylate; 1-dodecylthiol; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile; benzene; 8.1: Barbier reaction / 14.1: Mitsunobu reaction;
DOI:10.1021/ol2018533