Sodium Hydroxide → HCID 13849537, compound

HRID 978116Notes

Reaction equation

HRID 978116 reaction equation
Cl[C:2]1[C:3](=[O:15])[O:4][C:5]2[C:10]([C:11]=1[CH3:12])=[CH:9][C:8]([Cl:13])=[C:7]([OH:14])[CH:6]=2.[OH-:16].[Na+]>>[Cl:13][C:8]1[C:7]([OH:14])=[CH:6][C:5]2[O:4][C:2]([C:3]([OH:15])=[O:16])=[C:11]([CH3:12])[C:10]=2[CH:9]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 5410152HCID 5410152, compound

Product 1

HCID 13849537HCID 13849537, compoundYield 54%

Procedure

3-Chloro-4-methyl-6-chloro-7-hydroxycoumarin was refluxed with NaOH (30 ml, 1N) for 1 hour. The mixture was washed with three 50 ml portions of ethyl acetate. Then acidification (HCl, 3N) of the aqueous phase followed by filtration of the solid that precipitated gave 0.5 g (54% yield) of the desired acid, m.p. 279°-280° C. In the ethyl acetate extract 0.2 g of decarboxylate product was recovered as a by product,

Workup

  1. washThe mixture was washed with three 50 ml portions of ethyl acetate
  2. filtrationThen acidification (HCl, 3N) of the aqueous phase followed by filtration of the solid
  3. customthat precipitated

Sources & evidence

ORD record
ord-cc839381c885425785368040c31641c0
Source dataset
uspto-grants-1987_05
Patent number
US04663347

Reaction notes

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