Water → 4-(chloromethyl)-7-hydroxy-2H-chromen-2-one

HRID 1163290Notes

Reaction equation

HRID 1163290 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].O>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]=1

Participants

5

Reactant 3

HCID 962WaterHCID 5054ResorcinolHCID 69484Ethyl 4-chloroacetoacetate

Product 1

HCID 53988464-(chloromethyl)-7-hydroxy-2H-chromen-2-oneYield 84%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Ethyl 4-chloroacetoacetate (14.0 g, 85.0 mmol) was dissolved in conc. sulfuric acid (30 mL) under ice-cooling and 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 iced water. The resulting solid was collected by filtration, washed with water and air dried to give the title compound (14.1 g, 84%).

Workup

  1. temperaturecooling
  2. filtrationThe resulting solid was collected by filtration
  3. washwashed with water and air
  4. customdried

Sources & evidence

ORD record
ord-4736c57d5d4e4812b9350485875cd015
Source dataset
uspto-grants-2010_10
Patent number
US07820837B2

Reaction notes

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