(1R,8aS)-2-acetyloxy-5,5,8a-trimethyl-1,5,6,7,8,8a-hexahydro-naphthalene-1-carboxylic acid (-)-menthyl ester

Base Information

• Chemical Name: (1R,8aS)-2-acetyloxy-5,5,8a-trimethyl-1,5,6,7,8,8a-hexahydro-naphthalene-1-carboxylic acid (-)-menthyl ester
• CAS No.: 807360-59-4
• Molecular Formula: C₂₆H₄₀O₄
• Molecular Weight: 416.601

Synonyms:(1R,8aS)-2-acetyloxy-5,5,8a-trimethyl-1,5,6,7,8,8a-hexahydro-naphthalene-1-carboxylic acid (-)-menthyl ester

Chemical Property of (1R,8aS)-2-acetyloxy-5,5,8a-trimethyl-1,5,6,7,8,8a-hexahydro-naphthalene-1-carboxylic acid (-)-menthyl ester

Chemical Property:

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Technology Process of (1R,8aS)-2-acetyloxy-5,5,8a-trimethyl-1,5,6,7,8,8a-hexahydro-naphthalene-1-carboxylic acid (-)-menthyl ester

There total 2 articles about (1R,8aS)-2-acetyloxy-5,5,8a-trimethyl-1,5,6,7,8,8a-hexahydro-naphthalene-1-carboxylic acid (-)-menthyl 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:

3-acetyloxy-5-(2',6',6'-trimethylcyclohex-1'-enyl)-penta-2,4-dienoic acid (-)-menthyl ester → (1R,8aS)-2-acetyloxy-5,5,8a-trimethyl-1,5,6,7,8,8a-hexahydro-naphthalene-1-carboxylic acid (-)-menthyl ester (807360-59-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / benzanthrone / tetrahydrofuran / 8 h / Irradiation

2: 0.21 g / 1.5 h / 180 °C

With 7H-benz[d,e]anthracene-7-one; In tetrahydrofuran;

DOI:10.1016/j.tetasy.2004.07.064

Reference yield:

3-acetyloxy-5-(2',6',6'-trimethylcyclohex-1'-enyl)-penta-2,4-dienoic acid (-)-menthyl ester (807360-57-2) → (1R,8aS)-2-acetyloxy-5,5,8a-trimethyl-1,5,6,7,8,8a-hexahydro-naphthalene-1-carboxylic acid (-)-menthyl ester (807360-59-4) + (1S,8aR)-2-acetyloxy-5,5,8a-trimethyl-1,5,6,7,8,8a-hexahydro-naphthalene-1-carboxylic acid (-)-menthyl ester (807360-62-9)

Guidance literature:

at 180 ℃; for 1.5h;

DOI:10.1016/j.tetasy.2004.07.064

Reference yield:

(1R,8aS)-2-acetyloxy-5,5,8a-trimethyl-1,5,6,7,8,8a-hexahydro-naphthalene-1-carboxylic acid (-)-menthyl ester (807360-59-4) → (1R,2S,4aS,8aR)-2-Acetoxy-5,5,8a-trimethyl-decahydro-naphthalene-1-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 4h; under 1034.3 Torr;

DOI:10.1016/j.tetasy.2004.07.064

upstream raw materials:

3-acetyloxy-5-(2',6',6'-trimethylcyclohex-1'-enyl)-penta-2,4-dienoic acid (-)-menthyl ester

Downstream raw materials:

(4aR,8aS)-3,4,4aα,5,6,7,8,8aβ-octahydro-5,5,8aβ-trimethyl-2(1H)naphthalenone

(1R,2R,4aR,8aR)-(-)-1-hydroxymethyl-2-hydroxy-5,5,8a-trimethyldecahydronaphthalene

(1S,2S,4aS,8aR)-2-hydroxy-1-hydroxymethyl-5,5,8a-trimethyl-decahydronaphthalene

(1S,4aR,8aR)-5,5,8a-trimethyl-2-oxo-decahydro-naphthalene-1-carboxylic acid benzyl ester

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