4-Chlororesorcinol → 6-Chloro-7-hydroxy coumarin
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]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- filtrationThe solid is filtered
- washwashed with water
- customThe crude product is recrystallized from ethanol/chloroform
Sources & evidence
- ORD record
- ord-eeb1a068930844398b12dcfc3cf9e695
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07709664B2
Reaction notes
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