Hydrochloric Acid → 1-Hydroxy-3-(hydroxymethyl)-8-methoxyanthracene-9,10-dione

HRID 2058149Notes

Reaction equation

HRID 2058149 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:16]=1[C:15](=[O:17])[C:14]1[C:13]([O:18]C(=O)C)=[CH:12][C:11]([CH2:22][O:23]C(=O)C)=[CH:10][C:9]=1[C:8]2=[O:27].Cl.O>CO>[OH:18][C:13]1[C:14]2[C:15](=[O:17])[C:16]3[C:7](=[CH:6][CH:5]=[CH:4][C:3]=3[O:2][CH3:1])[C:8](=[O:27])[C:9]=2[CH:10]=[C:11]([CH2:22][OH:23])[CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 10406699HCID 10406699, compound

Product 1

HCID 233496281-Hydroxy-3-(hydroxymethyl)-8-methoxyanthracene-9,10-dioneYield 70.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The 8-methoxy-3-acetoxymethyl-1-acetoxy anthraquinone (120 mg) of Example 22 was refluxed in methanol (30 ml) with concentrated hydrochloric acid (10 ml) and water (10 ml) for three hours. The solvents and acid were evaporated off in vacuum and the residue crystallized from chloroform to obtain reddish yellow crystals (65 mg) of 1-hydroxy-3-hydroxymethyl-8-methoxy anthraquinone (formula 19). m.p. 215°-216°, ir (KBr) 3520-3460, 1670, 1635, 1585 cm-1.

Workup

  1. customThe solvents and acid were evaporated off in vacuum
  2. customthe residue crystallized from chloroform

Sources & evidence

ORD record
ord-7c77745ef05a4cd1b27c4521c52b6407
Source dataset
uspto-grants-1980_07
Patent number
US04215062

Reaction notes

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