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

HRID 1908888Notes

Reaction equation

HRID 1908888 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]=1

Participants

4

Reactant 2

HCID 5054ResorcinolHCID 69484Ethyl 4-chloroacetoacetate

Product 1

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

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

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

  1. temperatureUnder ice-cooling
  2. filtrationthe precipitated solid was collected by filtration
  3. washwashed with water
  4. customair-dried

Sources & evidence

ORD record
ord-f790e80f6ec94658bcd4119417d7edd3
Source dataset
uspto-grants-2013_12
Patent number
US08598226B2

Reaction notes

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