1-[6,13-Di-tert-butyl-16-(1-hydroxy-2-phenyl-ethyl)-tricyclo[9.3.1.1^4,8]hexadeca-1⁽¹⁴⁾,4,6,8⁽¹⁶⁾,11⁽¹⁵⁾,12-hexaen-15-yl]-2-phenyl-ethanol

Base Information

• Chemical Name: 1-[6,13-Di-tert-butyl-16-(1-hydroxy-2-phenyl-ethyl)-tricyclo[9.3.1.1^4,8]hexadeca-1⁽¹⁴⁾,4,6,8⁽¹⁶⁾,11⁽¹⁵⁾,12-hexaen-15-yl]-2-phenyl-ethanol
• CAS No.: 344415-49-2
• Molecular Formula: C₄₀H₄₈O₂
• Molecular Weight: 560.82

Synonyms:1-[6,13-Di-tert-butyl-16-(1-hydroxy-2-phenyl-ethyl)-tricyclo[9.3.1.1^4,8]hexadeca-1⁽¹⁴⁾,4,6,8⁽¹⁶⁾,11⁽¹⁵⁾,12-hexaen-15-yl]-2-phenyl-ethanol

Chemical Property of 1-[6,13-Di-tert-butyl-16-(1-hydroxy-2-phenyl-ethyl)-tricyclo[9.3.1.1^4,8]hexadeca-1⁽¹⁴⁾,4,6,8⁽¹⁶⁾,11⁽¹⁵⁾,12-hexaen-15-yl]-2-phenyl-ethanol

Chemical Property:

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Technology Process of 1-[6,13-Di-tert-butyl-16-(1-hydroxy-2-phenyl-ethyl)-tricyclo[9.3.1.1^4,8]hexadeca-1⁽¹⁴⁾,4,6,8⁽¹⁶⁾,11⁽¹⁵⁾,12-hexaen-15-yl]-2-phenyl-ethanol

There total 2 articles about 1-[6,13-Di-tert-butyl-16-(1-hydroxy-2-phenyl-ethyl)-tricyclo[9.3.1.1^4,8]hexadeca-1⁽¹⁴⁾,4,6,8⁽¹⁶⁾,11⁽¹⁵⁾,12-hexaen-15-yl]-2-phenyl-ethanol 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: 71.4%

phenylmagnesium bromide (1589-82-8) + 5,13-Di-tert-butyl-8,16-diformyl<2.2>metacyclophane (85151-93-5) → 1-[6,13-Di-tert-butyl-16-(1-hydroxy-2-phenyl-ethyl)-tricyclo[9.3.1.14,8]hexadeca-1(14),4,6,8(16),11(15),12-hexaen-15-yl]-2-phenyl-ethanol (344415-49-2)

Guidance literature:

In diethyl ether; for 12h; Heating;

DOI:10.1021/jo00157a015

Reference yield:

8,16-bis(pyridiniomethyl)-5,13-di-tert-butyl<2.2>metacyclophane dibromide (85201-29-2,78919-84-3) → 1-[6,13-Di-tert-butyl-16-(1-hydroxy-2-phenyl-ethyl)-tricyclo[9.3.1.14,8]hexadeca-1(14),4,6,8(16),11(15),12-hexaen-15-yl]-2-phenyl-ethanol (344415-49-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 57 percent / 1N aq. NaOH / ethanol; H₂O / 0.08 h / Ambient temperature

2: 93.5 percent / 5N aq. HCl / ethanol / Ambient temperature

3: 71.4 percent / diethyl ether / 12 h / Heating

With hydrogenchloride; sodium hydroxide; In diethyl ether; ethanol; water;

DOI:10.1021/jo00157a015

Reference yield: 89.0%

1-[6,13-Di-tert-butyl-16-(1-hydroxy-2-phenyl-ethyl)-tricyclo[9.3.1.14,8]hexadeca-1(14),4,6,8(16),11(15),12-hexaen-15-yl]-2-phenyl-ethanol (344415-49-2) → 6,13-Di-tert-butyl-15,16-bis-((E)-styryl)-tricyclo[9.3.1.14,8]hexadeca-1(14),4,6,8(16),11(15),12-hexaene (85152-31-4)

Guidance literature:

With hydrogenchloride; In acetic acid; for 0.5h; Heating;

DOI:10.1021/jo00157a015

upstream raw materials:

phenylmagnesium bromide

5,13-Di-tert-butyl-8,16-diformyl<2.2>metacyclophane

8,16-bis(pyridiniomethyl)-5,13-di-tert-butyl<2.2>metacyclophane dibromide

Downstream raw materials:

6,13-Di-tert-butyl-15,16-bis-((E)-styryl)-tricyclo[9.3.1.1^4,8]hexadeca-1⁽¹⁴⁾,4,6,8⁽¹⁶⁾,11⁽¹⁵⁾,12-hexaene

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