Water → HCID 13050866, compound

HRID 1648954Notes

Reaction equation

HRID 1648954 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-7badf1e4d6644f87bcc0ba23c01dce3e
Source dataset
uspto-grants-1983_11
Patent number
US04414226

Reaction notes

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