2-[2-hydroxymethyl-6-(2-methyl-allyloxy)-benzoyl]-5-methyl-4,4-bis-(3-methyl-but-2-enyl)-cyclohexane-1,3-dione

Base Information

Chemical Name:2-[2-hydroxymethyl-6-(2-methyl-allyloxy)-benzoyl]-5-methyl-4,4-bis-(3-methyl-but-2-enyl)-cyclohexane-1,3-dione
CAS No.:857652-21-2
Molecular Formula:C₂₉H₃₈O₅
Molecular Weight:466.618
Hs Code.:

Synonyms:2-[2-hydroxymethyl-6-(2-methyl-allyloxy)-benzoyl]-5-methyl-4,4-bis-(3-methyl-but-2-enyl)-cyclohexane-1,3-dione

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Chemical Property of 2-[2-hydroxymethyl-6-(2-methyl-allyloxy)-benzoyl]-5-methyl-4,4-bis-(3-methyl-but-2-enyl)-cyclohexane-1,3-dione

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Technology Process of 2-[2-hydroxymethyl-6-(2-methyl-allyloxy)-benzoyl]-5-methyl-4,4-bis-(3-methyl-but-2-enyl)-cyclohexane-1,3-dione

There total 12 articles about 2-[2-hydroxymethyl-6-(2-methyl-allyloxy)-benzoyl]-5-methyl-4,4-bis-(3-methyl-but-2-enyl)-cyclohexane-1,3-dione 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: 64.0%

: 4-bromo-benzoic acid 2-[2-hydroxy-4-methyl-3,3-bis-(3-methyl-but-2-enyl)-6-oxo-cyclohex-1-enecarbonyl]-3-(2-methyl-allyloxy)-benzyl ester

: 857652-21-2
2-[2-hydroxymethyl-6-(2-methyl-allyloxy)-benzoyl]-5-methyl-4,4-bis-(3-methyl-but-2-enyl)-cyclohexane-1,3-dione

Guidance literature:: 4-bromo-benzoic acid 2-[2-hydroxy-4-methyl-3,3-bis-(3-methyl-but-2-enyl)-6-oxo-cyclohex-1-enecarbonyl]-3-(2-methyl-allyloxy)-benzyl ester; With potassium carbonate; In methanol; at 25 ℃; for 12h;

With potassium carbonate; In methanol; at 25 ℃; for 0.5h;
DOI:10.1021/ja0509984

Reference yield:

: 112429-70-6
(2,2-dimethyl-4H-benzo[d][1,3]dioxin-5-yl)methanol

: 857652-21-2
2-[2-hydroxymethyl-6-(2-methyl-allyloxy)-benzoyl]-5-methyl-4,4-bis-(3-methyl-but-2-enyl)-cyclohexane-1,3-dione

Guidance literature:: Multi-step reaction with 8 steps

1.1: 97 percent / 4-(dimethylamino)pyridine; Et₃N / CH₂Cl₂ / 0.33 h / 25 °C

2.1: 85 percent / aq. p-TsOH / tetrahydrofuran / 10 h / 75 °C

3.1: 87 percent / MnO₂ / ethyl acetate / 1.5 h / 25 °C

4.1: 91 percent / K₂CO₃ / acetone / 2 h / 56 °C

5.1: 82 percent / toluene / 0 - 25 °C

6.1: 73 percent / pyridinium chlorochromate / CH₂Cl₂ / 12 h / 40 °C

7.1: 86 percent / Et₃N; 4-(dimethylamino)pyridine / tetrahydrofuran / 25 °C

8.1: K₂CO₃ / methanol / 12 h / 25 °C

8.2: 64 percent / aq. K₂CO₃ / methanol / 0.5 h / 25 °C

With dmap; manganese(IV) oxide; potassium carbonate; toluene-4-sulfonic acid; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; acetone; toluene;
DOI:10.1021/ja0509984

Reference yield:

: 870-63-3
prenyl bromide

: 857652-21-2
2-[2-hydroxymethyl-6-(2-methyl-allyloxy)-benzoyl]-5-methyl-4,4-bis-(3-methyl-but-2-enyl)-cyclohexane-1,3-dione

Guidance literature:: Multi-step reaction with 4 steps

1.1: LDA; HMPA / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 89 percent / tetrahydrofuran; hexane / 12 h / -78 - 20 °C

2.1: 95 percent / aq. HCl / tetrahydrofuran / 14 h / 25 °C

3.1: 86 percent / Et₃N; 4-(dimethylamino)pyridine / tetrahydrofuran / 25 °C

4.1: K₂CO₃ / methanol / 12 h / 25 °C

4.2: 64 percent / aq. K₂CO₃ / methanol / 0.5 h / 25 °C

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; potassium carbonate; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane;
DOI:10.1021/ja0509984