Water → 8-Acetoxy-10-chloro-9-hydroxy-1,4-anthracenedione

HRID 620901Notes

Reaction equation

HRID 620901 reaction equation
[Cl:1][C:2]1[C:15]2[C:10](=[C:11]([OH:16])[CH:12]=[CH:13][CH:14]=2)[C:9]([OH:17])=[C:8]2[C:3]=1[C:4](=[O:19])[CH:5]=[CH:6][C:7]2=[O:18].O.[O:21]1CC[CH2:23][CH2:22]1>C(OC(=O)C)(=O)C.N1C=CC=CC=1>[C:22]([O:16][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:10]=1[C:9]([OH:17])=[C:8]1[C:3]([C:4](=[O:19])[CH:5]=[CH:6][C:7]1=[O:18])=[C:2]2[Cl:1])(=[O:21])[CH3:23]

Participants

6

Reactant 3

HCID 962WaterHCID 8028TetrahydrofuranHCID 1366779410-Chloro-8,9-dihydroxy-1,4-anthracenedione2×

Product 1

HCID 110344498-Acetoxy-10-chloro-9-hydroxy-1,4-anthracenedione

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 7918Acetic AnhydrideCatalyst

Procedure

10-Chloro-8,9-dihydroxy-1,4-anthracenedione (compound 3) (180 mg) was dissolved with stirring in dry tetrahydrofuran (15 ml) at room temperature. Acetic anhydride (20 drops) and pyridine (15 drops) were added to the solution which was then stirred for 48 h. Acidified water was added and the suspension was extracted with dichloromethane. The combined organic layers were dried and evaporated, and the residue was column chromatographed on silica gel 60 (100 g) with chloroform/acetone mixture as the eluant. The major red band gave the product (compound 4) as a red solid (177 mg, 85%).

Workup

  1. extractionthe suspension was extracted with dichloromethane
  2. customThe combined organic layers were dried
  3. customevaporated
  4. customchromatographed on silica gel 60 (100 g) with chloroform/acetone mixture as the eluant

Sources & evidence

ORD record
ord-c7b4992f2a4d477c879ebddef80de30b
Source dataset
uspto-grants-1989_04
Patent number
US04822873

Reaction notes

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