10-benzyl-5,6-dibenzyloxy-1-hydroxy-3-methoxy-9(10H)-acridone

Base Information

• Chemical Name: 10-benzyl-5,6-dibenzyloxy-1-hydroxy-3-methoxy-9(10H)-acridone
• CAS No.: 149220-92-8
• Molecular Formula: C₃₅H₂₉NO₅
• Molecular Weight: 543.619
• Mol file: 149220-92-8.mol

Synonyms:

Chemical Property of 10-benzyl-5,6-dibenzyloxy-1-hydroxy-3-methoxy-9(10H)-acridone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 10-benzyl-5,6-dibenzyloxy-1-hydroxy-3-methoxy-9(10H)-acridone

There total 13 articles about 10-benzyl-5,6-dibenzyloxy-1-hydroxy-3-methoxy-9(10H)-acridone 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:

3,4-Dihydroxybenzoic acid (99-50-3) → 10-benzyl-5,6-dibenzyloxy-1-hydroxy-3-methoxy-9(10H)-acridone (149220-92-8)

Guidance literature:

Multi-step reaction with 11 steps

1: 58 percent / Et₃N / dimethylformamide / 15 h / Ambient temperature

2: 90 percent / 1 N aq. NaOH / ethanol / 2 h / 50 °C

3: Et₃N / dimethylformamide / 0.5 h / 0 °C

4: Et₃N / H₂O; dimethylformamide / 15 h / Ambient temperature

5: 1.) tert-BuLi, TMEDA, 2.) I₂ / 1.) hexane, THF, -70 deg C, 1 h, 2.) hexane, THF, -70 deg C, 1 h

6: 54 percent / CuCl, K₂CO₃ / propan-2-ol / 14 h / Heating

7: 1 N aq. HCl / methanol / 1 h

8: K₂CO₃ / propan-2-ol / 2 h / Heating

9: 1.) POCl₃, 2.) 1 N aq. HCl / 1.) reflux, 8 min, 2.) MeOH, 60 deg C, 30 min

10: 1.) KOH / 1.) DMSO, RT, 30 min, 2.) DMSO, 50 deg C, 1 h

11: 1.) BF₃*Et₂O, 2.) LiBr, 3.) MeOH

With hydrogenchloride; methanol; potassium hydroxide; sodium hydroxide; N,N,N,N,-tetramethylethylenediamine; boron trifluoride diethyl etherate; iodine; tert.-butyl lithium; potassium carbonate; triethylamine; copper(l) chloride; lithium bromide; trichlorophosphate; In methanol; ethanol; water; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1248/cpb.41.445

Reference yield:

benzyl chloride (100-44-7) → 10-benzyl-5,6-dibenzyloxy-1-hydroxy-3-methoxy-9(10H)-acridone (149220-92-8)

Guidance literature:

Multi-step reaction with 4 steps

1: K₂CO₃ / propan-2-ol / 2 h / Heating

2: 1.) POCl₃, 2.) 1 N aq. HCl / 1.) reflux, 8 min, 2.) MeOH, 60 deg C, 30 min

3: 1.) KOH / 1.) DMSO, RT, 30 min, 2.) DMSO, 50 deg C, 1 h

4: 1.) BF₃*Et₂O, 2.) LiBr, 3.) MeOH

With hydrogenchloride; methanol; potassium hydroxide; boron trifluoride diethyl etherate; potassium carbonate; lithium bromide; trichlorophosphate; In isopropyl alcohol;

DOI:10.1248/cpb.41.445

Reference yield:

3,4-bis(methoxymethoxy)benzoic acid (149220-87-1) → 10-benzyl-5,6-dibenzyloxy-1-hydroxy-3-methoxy-9(10H)-acridone (149220-92-8)

Guidance literature:

Multi-step reaction with 9 steps

1: Et₃N / dimethylformamide / 0.5 h / 0 °C

2: Et₃N / H₂O; dimethylformamide / 15 h / Ambient temperature

3: 1.) tert-BuLi, TMEDA, 2.) I₂ / 1.) hexane, THF, -70 deg C, 1 h, 2.) hexane, THF, -70 deg C, 1 h

4: 54 percent / CuCl, K₂CO₃ / propan-2-ol / 14 h / Heating

5: 1 N aq. HCl / methanol / 1 h

6: K₂CO₃ / propan-2-ol / 2 h / Heating

7: 1.) POCl₃, 2.) 1 N aq. HCl / 1.) reflux, 8 min, 2.) MeOH, 60 deg C, 30 min

8: 1.) KOH / 1.) DMSO, RT, 30 min, 2.) DMSO, 50 deg C, 1 h

9: 1.) BF₃*Et₂O, 2.) LiBr, 3.) MeOH

With hydrogenchloride; methanol; potassium hydroxide; N,N,N,N,-tetramethylethylenediamine; boron trifluoride diethyl etherate; iodine; tert.-butyl lithium; potassium carbonate; triethylamine; copper(l) chloride; lithium bromide; trichlorophosphate; In methanol; water; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1248/cpb.41.445

upstream raw materials:

10-benzyl-5,6-dibenzyloxy-1,3-dimethoxy-9(10H)-acridone

3,4-Dihydroxybenzoic acid

benzyl chloride

3,4-bis(methoxymethoxy)benzoic acid