1,2,3,4,4a,5,6,7,8,8a-decahydro-2-hydroxy-2,5,5,8a-tetramethyl-1-naphthaleneethanol

Base Information

• Chemical Name: 1,2,3,4,4a,5,6,7,8,8a-decahydro-2-hydroxy-2,5,5,8a-tetramethyl-1-naphthaleneethanol
• CAS No.: 335193-14-1
• Molecular Formula: C₁₆H₃₀O₂
• Molecular Weight: 254.413

Synonyms:1,2,3,4,4a,5,6,7,8,8a-decahydro-2-hydroxy-2,5,5,8a-tetramethyl-1-naphthaleneethanol

Chemical Property of 1,2,3,4,4a,5,6,7,8,8a-decahydro-2-hydroxy-2,5,5,8a-tetramethyl-1-naphthaleneethanol

Chemical Property:

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Technology Process of 1,2,3,4,4a,5,6,7,8,8a-decahydro-2-hydroxy-2,5,5,8a-tetramethyl-1-naphthaleneethanol

There total 2 articles about 1,2,3,4,4a,5,6,7,8,8a-decahydro-2-hydroxy-2,5,5,8a-tetramethyl-1-naphthaleneethanol 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: 91.0%

(3aR)-(+)-sclareolide (564-20-5,1216-84-8,30450-17-0,58976-28-6,64090-92-2,67844-42-2,79768-41-5,79768-42-6,86688-27-9,86688-28-0,95406-08-9,98719-44-9,98719-46-1,131831-65-7,140851-80-5) → 1,2,3,4,4a,5,6,7,8,8a-decahydro-2-hydroxy-2,5,5,8a-tetramethyl-1-naphthaleneethanol (335193-14-1)

Guidance literature:

With potassium methanolate; hydrogen; dichloro-bis-[2-(diphenylphosphino)ethylamine]ruthenium; In toluene; at 100 ℃; for 6h; under 22502.3 Torr; Product distribution / selectivity;

Reference yield: 81.0%

3,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethylspiro-1-ethanol (123522-41-8,124578-48-9,124578-49-0,124578-50-3,124578-51-4) → 1,2,3,4,4a,5,6,7,8,8a-decahydro-2-hydroxy-2,5,5,8a-tetramethyl-1-naphthaleneethanol (335193-14-1)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 3h; Ambient temperature;

Reference yield:

1,2,3,4,4a,5,6,7,8,8a-decahydro-2-hydroxy-2,5,5,8a-tetramethyl-1-naphthaleneethanol (335193-14-1) → C42H57BrNOSi(1+)*CF3O3S(1-)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine; methanesulfonyl chloride / toluene / 1 h / 0 °C / Inert atmosphere

1.2: 5 h / 0 - 40 °C / Inert atmosphere

1.3: 9 h / 22 °C / Inert atmosphere

2.1: 2-fluoropyridine / 1,2-dichloro-ethane / 30 h / -40 - -10 °C / Inert atmosphere

With 2-fluoropyridine; methanesulfonyl chloride; triethylamine; In 1,2-dichloro-ethane; toluene;

DOI:10.1002/anie.202100288

upstream raw materials:

3,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethylspiro-1-ethanol

(3aR)-(+)-sclareolide

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