Water → HCID 13050866, compound

HRID 371303Notes

Reaction equation

HRID 371303 reaction equation
[CH3:1][O:2][C:3]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[OH:14])[C:5](=[O:15])[C:4]=1[C:16]1[C:25]([O:26][CH3:27])=[CH:24][C:23]([CH3:28])=[CH:22][C:17]=1[C:18]([O:20][CH3:21])=[O:19].[C:29](OC(=O)C)(=[O:31])[CH3:30].O>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[O:14][C:29](=[O:31])[CH3:30])[C:5](=[O:15])[C:4]=1[C:16]1[C:25]([O:26][CH3:27])=[CH:24][C:23]([CH3:28])=[CH:22][C:17]=1[C:18]([O:20][CH3:21])=[O:19]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 13231986HCID 13231986, compound

Product 1

HCID 13050866HCID 13050866, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In pyridine (3 ml) was dissolved methyl 2-(3-methoxy-5-hydroxy-1,4-naphthoquinon-2-yl)-3-methoxy-5-methylbenzoate (20 mg) as obtained in Example 3, followed by addition of acetic anhydride (3 ml). The mixture was allowed to stand at room temperature overnight. After addition of water, the mixture was extracted with ethyl acetate. The solvent layer was washed with dilute HCl, water and dilute aqueous sodium hydrogen carbonate in that order, and dried over magnesium sulfate. The solvent was then distilled off and the residue was crystallized by addition of methanol. The above procedure gave methyl 2-(3-methoxy-5-acetoxy-1,4-naphthoquinon-2-yl)-3-methoxy-5-methylbenzoate (13 mg).

Workup

  1. customas obtained in Example 3
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe solvent layer was washed with dilute HCl, water and dilute aqueous sodium hydrogen carbonate in that order
  4. dry with materialdried over magnesium sulfate
  5. distillationThe solvent was then distilled off
  6. customthe residue was crystallized by addition of methanol

Sources & evidence

ORD record
ord-0b8f839dee8246b488d89ac2882bcd3d
Source dataset
uspto-grants-1985_07
Patent number
US04530845

Reaction notes

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