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

HRID 2234236

Reaction equation

HRID 2234236 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-eeb1a068930844398b12dcfc3cf9e695
Source dataset
uspto-grants-2010_05
Patent number
US07709664B2

Linked notes

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