6,6-dimethyl-4-hydroxytetrahydrobenzofuran

Base Information

• Chemical Name: 6,6-dimethyl-4-hydroxytetrahydrobenzofuran
• CAS No.: 160805-71-0
• Molecular Formula: C₁₀H₁₄O₂
• Molecular Weight: 166.22
• Mol file: 160805-71-0.mol

Synonyms:6,6-dimethyl-4-hydroxytetrahydrobenzofuran

Chemical Property of 6,6-dimethyl-4-hydroxytetrahydrobenzofuran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6,6-dimethyl-4-hydroxytetrahydrobenzofuran

There total 1 articles about 6,6-dimethyl-4-hydroxytetrahydrobenzofuran 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: 5.0%

4-oxo-6,6-dimethyl-4,5,6,7-tetrahydrobenzofuran (76230-27-8) → 6,6-dimethyl-4-hydroxytetrahydrobenzofuran (160805-71-0) + 5,5-dimethyl-2-(2-hydroxyethyl)cyclohexanol + 3,3,6,6-tetramethyl-1,2,3,4,5,6,7,8-octahydrophenanthrene-1,8-dione + bis 4,4'-<6,6-dimethyl-4-hydroxytetrahydrobenzofuran>

Guidance literature:

With methanol; sodium; at -33 ℃; for 1h; Further byproducts given;

DOI:10.1002/jhet.5570350608

Reference yield: 99.0%

benzyl bromide (100-39-0) + 6,6-dimethyl-4-hydroxytetrahydrobenzofuran (160805-71-0) → 4-Benzyloxy-6,6-dimethyl-4,5,6,7-tetrahydro-benzofuran (160805-61-8)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; Ambient temperature;

DOI:10.1039/c39940001979

Reference yield:

6,6-dimethyl-4-hydroxytetrahydrobenzofuran (160805-71-0) → Toluene-4-sulfonic acid (4aS,5S,8aS)-4a,8a-dihydroxy-7,7-dimethyl-4,4a,5,6,7,8,8a,9-octahydro-naphtho[2,3-c]furan-5-yl ester

Guidance literature:

Multi-step reaction with 10 steps

1: 99 percent / NaH / dimethylformamide / Ambient temperature

2: 95 percent / POCl₃ / Ambient temperature

3: NaBH₄ / ethanol / Ambient temperature

4: 98 percent / aq. NaOH / Bu₄NHSO₄ / diethyl ether / Ambient temperature

5: tBuOK / 2-methyl-propan-2-ol / 70 °C

6: Li / liquid ammonia; tetrahydrofuran / -78 °C

7: 46 percent / PDC / CH₂Cl₂ / Ambient temperature

8: 85 percent / DIBAH / tetrahydrofuran / -78 °C

9: 33 percent / OsO₄ / CH₂Cl₂; pyridine / Ambient temperature

10: 80 percent / DMAP, NEt₃ / CH₂Cl₂ / 40 °C

With dmap; sodium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; dipyridinium dichromate; potassium tert-butylate; lithium; sodium hydride; diisobutylaluminium hydride; triethylamine; trichlorophosphate; tetra(n-butyl)ammonium hydrogensulfate; In tetrahydrofuran; pyridine; diethyl ether; ethanol; dichloromethane; ammonia; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1039/c39940001979

upstream raw materials:

4-oxo-6,6-dimethyl-4,5,6,7-tetrahydrobenzofuran

Downstream raw materials:

4-Benzyloxy-6,6-dimethyl-4,5,6,7-tetrahydro-benzofuran

4-Benzyloxy-6,6-dimethyl-4,5,6,7-tetrahydro-benzofuran-2-carbaldehyde

(4-Benzyloxy-6,6-dimethyl-4,5,6,7-tetrahydro-benzofuran-2-yl)-methanol

4-Benzyloxy-6,6-dimethyl-2-prop-2-ynyloxymethyl-4,5,6,7-tetrahydro-benzofuran