Acetic Acid → HCID 13231986, compound

HRID 1648947Notes

Reaction equation

HRID 1648947 reaction equation
O[C:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[OH:13])[C:4](=[O:14])[C:3]=1[C:15]1[C:23]([O:24][CH3:25])=[CH:22][C:21]([CH3:26])=[CH:20][C:16]=1[C:17]([OH:19])=[O:18].[N+](=[CH2:29])=[N-].C(O)(=O)C.[CH3:34][OH:35]>>[CH3:34][O:35][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[OH:13])[C:4](=[O:14])[C:3]=1[C:15]1[C:23]([O:24][CH3:25])=[CH:22][C:21]([CH3:26])=[CH:20][C:16]=1[C:17]([O:19][CH3:29])=[O:18]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 9550Diazomethane2×HCID 178490201HCID 178490201, compound

Product 1

HCID 13231986HCID 13231986, compound

Procedure

2-(3,5-Dihydroxy-1,4-naphthoquinon-2-yl)-3-methoxy-5-methylbenzoic acid (100 mg) was dissolved in methanol (20 ml) and treated with diazomethane at room temperature. After 2 hours of reaction, the excess diazomethane was decomposed with acetic acid, the solvent was distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography, elution being carried out with chloroform. The above procedure gave methyl 2-(3-methoxy-5-hydroxy-1,4-naphthoquinon-2-yl)-3-methoxy-5-methylbenzoate (60 mg).

Workup

  1. customAfter 2 hours of reaction
  2. distillationthe solvent was distilled off under reduced pressure
  3. washthe residue was subjected to silica gel column chromatography, elution

Sources & evidence

ORD record
ord-616e0fdbe0cf44b9bd8603b369f29dd5
Source dataset
uspto-grants-1983_11
Patent number
US04414226

Reaction notes

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