5-(3,5-Bis-methoxymethoxy-benzoyl)-3-methoxymethoxy-9-methyl-8,13-dioxa-tricyclo[7.3.1.0^2,7]trideca-2⁽⁷⁾,3,5-triene-4-carbaldehyde

Base Information

• Chemical Name: 5-(3,5-Bis-methoxymethoxy-benzoyl)-3-methoxymethoxy-9-methyl-8,13-dioxa-tricyclo[7.3.1.0^2,7]trideca-2⁽⁷⁾,3,5-triene-4-carbaldehyde
• CAS No.: 116387-07-6
• Molecular Formula: C₂₆H₃₀O₁₀
• Molecular Weight: 502.518

Synonyms:5-(3,5-Bis-methoxymethoxy-benzoyl)-3-methoxymethoxy-9-methyl-8,13-dioxa-tricyclo[7.3.1.0^2,7]trideca-2⁽⁷⁾,3,5-triene-4-carbaldehyde

Chemical Property of 5-(3,5-Bis-methoxymethoxy-benzoyl)-3-methoxymethoxy-9-methyl-8,13-dioxa-tricyclo[7.3.1.0^2,7]trideca-2⁽⁷⁾,3,5-triene-4-carbaldehyde

Chemical Property:

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Technology Process of 5-(3,5-Bis-methoxymethoxy-benzoyl)-3-methoxymethoxy-9-methyl-8,13-dioxa-tricyclo[7.3.1.0^2,7]trideca-2⁽⁷⁾,3,5-triene-4-carbaldehyde

There total 12 articles about 5-(3,5-Bis-methoxymethoxy-benzoyl)-3-methoxymethoxy-9-methyl-8,13-dioxa-tricyclo[7.3.1.0^2,7]trideca-2⁽⁷⁾,3,5-triene-4-carbaldehyde 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: 80.6%

(3,5-Bis-methoxymethoxy-phenyl)-(4-hydroxymethyl-3-methoxymethoxy-9-methyl-8,13-dioxa-tricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-5-yl)-methanol (116387-06-5,116499-01-5) → 5-(3,5-Bis-methoxymethoxy-benzoyl)-3-methoxymethoxy-9-methyl-8,13-dioxa-tricyclo[7.3.1.02,7]trideca-2(7),3,5-triene-4-carbaldehyde (116387-07-6)

Guidance literature:

With sodium acetate; pyridinium chlorochromate; In dichloromethane; for 1h;

Reference yield:

ethylene-cetal de la bromo-5 pentanone-2 (24400-75-7) → 5-(3,5-Bis-methoxymethoxy-benzoyl)-3-methoxymethoxy-9-methyl-8,13-dioxa-tricyclo[7.3.1.02,7]trideca-2(7),3,5-triene-4-carbaldehyde (116387-07-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) ether, -10 deg C, 3 h, 2.) ether, THF, -10 deg C, 1 h

2: 67.1 percent / conc.sulphuric acid / aq. acetic acid / 26 h

3: 1.) BuLi / 1.) ether, hexane, 2.5 h, 2.) ether, hexane, 30 min

4: 1.) TMEDA, s-BuLi / 1.) THF, cyclohexane, -78 deg C, 7 min, 2.) THF,cyclohexane, -78 deg C, 45 min

5: 88.6 percent / 2M sulphuric acid / tetrahydrofuran; H₂O / 24 h

6: 96.7 percent / LiAlH₄ / tetrahydrofuran / 1 h

7: 80.6 percent / PCC, sodium acetate / CH₂Cl₂ / 1 h

With tetrahydrofuran; lithium aluminium tetrahydride; n-butyllithium; diethyl ether; N,N,N,N,-tetramethylethylenediamine; sulfuric acid; sec.-butyllithium; sodium acetate; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; water; acetic acid;

Reference yield:

bromo-5-pentanone-2 (3884-71-7) → 5-(3,5-Bis-methoxymethoxy-benzoyl)-3-methoxymethoxy-9-methyl-8,13-dioxa-tricyclo[7.3.1.02,7]trideca-2(7),3,5-triene-4-carbaldehyde (116387-07-6)

Guidance literature:

Multi-step reaction with 8 steps

1: toluene-p-sulphonic acid hydrate / benzene / 2 h / Heating

2: 1.) ether, -10 deg C, 3 h, 2.) ether, THF, -10 deg C, 1 h

3: 67.1 percent / conc.sulphuric acid / aq. acetic acid / 26 h

4: 1.) BuLi / 1.) ether, hexane, 2.5 h, 2.) ether, hexane, 30 min

5: 1.) TMEDA, s-BuLi / 1.) THF, cyclohexane, -78 deg C, 7 min, 2.) THF,cyclohexane, -78 deg C, 45 min

6: 88.6 percent / 2M sulphuric acid / tetrahydrofuran; H₂O / 24 h

7: 96.7 percent / LiAlH₄ / tetrahydrofuran / 1 h

8: 80.6 percent / PCC, sodium acetate / CH₂Cl₂ / 1 h

With tetrahydrofuran; lithium aluminium tetrahydride; n-butyllithium; diethyl ether; N,N,N,N,-tetramethylethylenediamine; sulfuric acid; sec.-butyllithium; sodium acetate; toluene-4-sulfonic acid; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; water; acetic acid; benzene;

upstream raw materials:

(3,5-Bis-methoxymethoxy-phenyl)-(4-hydroxymethyl-3-methoxymethoxy-9-methyl-8,13-dioxa-tricyclo[7.3.1.0^2,7]trideca-2⁽⁷⁾,3,5-trien-5-yl)-methanol

ethylene-cetal de la bromo-5 pentanone-2

bromo-5-pentanone-2

1,3-bis(methoxymethyl)resorcinol

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