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

HRID 922249Notes

Reaction equation

HRID 922249 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 78.3%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a 250 mL RB flask fitted with magnetic stirrer was charged with Ethyl 4-chloroacetoacetate (22.12 g, 134.9 mmol) was dissolved in concentrated sulfuric acid (48 mL) at 0° C., and resorcinol (14.0 g, 127.3 mmol) was added portionwise. The mixture was stirred at room temperature for 2 h. The reaction mixture was poured into ice-water, and the resulting solid was collected by filtration, washed with water, and dried to give 4-(chloromethyl)-7-hydroxy-2H-chromen-2-one (21.0 g, 75.6%) as a beige solid.

Workup

  1. customTo a 250 mL RB flask fitted with magnetic stirrer
  2. filtrationthe resulting solid was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-68abbfb5ccfe44748ecb2d7ac9bf9552
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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