4-Chlororesorcinol → 6-Chloro-7-hydroxy coumarin

HRID 1671491

Reaction equation

HRID 1671491 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][C:3]=1[OH:9].[CH2:10]([CH:17](C(C)=O)[C:18](OCC)=[O:19])C1C=CC=CC=1>OS(O)(=O)=O>[Cl:1][C:2]1[CH:8]=[C:7]2[C:5](=[CH:4][C:3]=1[OH:9])[O:6][C:18](=[O:19])[CH:17]=[CH:10]2

Participants

4

Reactant 2

HCID 17314-ChlororesorcinolHCID 246929Ethyl alpha-benzylacetoacetate

Product 1

HCID 53931666-Chloro-7-hydroxy coumarinYield 104.9%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

4-Chlororesorcinol (26.25 g, 0.182 mol) and ethyl 2-benzylacetoacetate (40 g, 0.182 mol) are mixed in 70% H2SO4 (350 mL) at 0° C. The reaction mixture is stirred at room temperature for 72 hours and poured into ice water. The solid is filtered and washed with water. The crude product is recrystallized from ethanol/chloroform to afford 6-chloro-7-hydroxy coumarin intermediate (37.52 g, 68.7%).

Workup

  1. filtrationThe solid is filtered
  2. washwashed with water
  3. customThe crude product is recrystallized from ethanol/chloroform

Sources & evidence

ORD record
ord-b365926c56ad41a4b5dea9adf27d3d2b
Source dataset
uspto-grants-2011_08
Patent number
US07994318B2

Linked notes

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