Diethyl Ether → HCID 11142708, compound

HRID 1648951Notes

Reaction equation

HRID 1648951 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:25])[CH:5]=[C:6]([C:13]1[C:21]([O:22][CH3:23])=[CH:20][C:19]([CH3:24])=[CH:18][C:14]=1[C:15]([OH:17])=[O:16])[C:7]2=[O:12].[CH2:26](OCC)C.[N+](=C)=[N-]>CO>[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:25])[CH:5]=[C:6]([C:13]1[C:21]([O:22][CH3:23])=[CH:20][C:19]([CH3:24])=[CH:18][C:14]=1[C:15]([O:17][CH3:26])=[O:16])[C:7]2=[O:12]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 9550DiazomethaneHCID 156388WS-5995 B

Product 1

HCID 11142708HCID 11142708, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In methanol (50 ml) was dissolved 2-(5-hydroxy-1,4-naphthoquinon-2-yl)-3-methoxy-5-methylbenzoic acid (1 g) as obtained in Example 15, followed by addition of a diethyl ether solution of diazomethane (20 ml). The mixture was allowed to stand at room temperature for an hour, after which the diethyl ether and methanol were distilled off. The residue was subjected to silical gel chromatography and recrystallized from diethyl ether-n-hexane. The procedure yielded yellow crystals (500 mg) of methyl 2-(5-hydroxy-1,4-naphthoquinon-2-yl)-3-methoxy-5-methylbenzoate.

Workup

  1. customas obtained in Example 15
  2. waitto stand at room temperature for an hour
  3. distillationafter which the diethyl ether and methanol were distilled off
  4. customrecrystallized from diethyl ether-n-hexane

Sources & evidence

ORD record
ord-de2411a98e154f69b9c1c5aa538b0758
Source dataset
uspto-grants-1983_11
Patent number
US04414226

Reaction notes

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