Resorcinol → 4-(chloromethyl)-7-hydroxy-2H-chromen-2-one
Reaction equation
[Cl:1][CH2:2][C:3](=O)[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[C:11]1([CH:18]=CC=[C:14](O)[CH:13]=1)[OH:12]>S(=O)(=O)(O)O>[Cl:1][CH2:2][C:3]1[C:9]2[C:8](=[CH:18][C:11]([OH:12])=[CH:13][CH:14]=2)[O:7][C:5](=[O:6])[CH:4]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Under ice-cooling, ethyl 4-chloroacetoacetate (14.0 g, 85.0 mmol) was dissolved in concentrated sulfuric acid (30 mL), resorcinol (8.81 g, 80.0 mmol) was added by small portions, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was poured into ice water, and the precipitated solid was collected by filtration, washed with water, and air-dried to give the title compound (14.1 g, yield 84%) as a beige powder.
Workup
- temperatureUnder ice-cooling
- filtrationthe precipitated solid was collected by filtration
- washwashed with water
- customair-dried
Sources & evidence
- ORD record
- ord-fe0b5de1698444ec8b5a4db7374edae3
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07732626B2
Reaction notes
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