Methanol → HCID 21191994, compound

HRID 1957804Notes

Reaction equation

HRID 1957804 reaction equation
[CH2:1]([O:8][C:9]1[C:18]([C:19]([O:21]C)=[O:20])=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:23]([O:25]C)=[O:24])[CH:15]=2)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.[OH-].[Na+]>O>[CH2:1]([O:8][C:9]1[C:18]([C:19]([OH:21])=[O:20])=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:23]([OH:25])=[O:24])[CH:15]=2)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 21191971HCID 21191971, compound

Product 1

HCID 21191994HCID 21191994, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

2-Benzyloxy-3,6-di-methoxycarbonylnaphthalene (0.52 g) obtained in Example 32 was dissolved in N-methyl-2-pyrrodidone (10 g) and methanol (10 g) and water (20 g) were added. Furthermore, an aqueous 1N-sodium hydroxide (4.5 g) was added, followed by stirring at about 60° C. for 2 hours. After the insoluble formed during the reaction was removed by filtration, the solution was adjusted to about pH 4 using aqueous 10% hydrochloric acid. The deposit was filtered and then washed with water to obtain 0.41 g of 2-benzyloxy-3,6-di-hydroxycarbonylnaphthalene as pale brown powder (DSC analysis value: 241.3° C.).

Workup

  1. customAfter the insoluble formed during the reaction
  2. customwas removed by filtration
  3. filtrationThe deposit was filtered
  4. washwashed with water

Sources & evidence

ORD record
ord-bb15f4a3b5d044eabb510558cabafe02
Source dataset
uspto-grants-1998_07
Patent number
US05786523

Reaction notes

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