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

HRID 1848763Notes

Reaction equation

HRID 1848763 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].[Cl:9][CH2:10][C:11](=O)[CH2:12][C:13](OCC)=[O:14].S(=O)(=O)(O)O.O>C(O)(=O)C>[Cl:9][CH2:10][C:11]1[C:8]2[C:1](=[CH:3][C:4]([OH:5])=[CH:6][CH:7]=2)[O:2][C:13](=[O:14])[CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 5054Resorcinol2×HCID 69484Ethyl 4-chloroacetoacetate

Product 1

HCID 53988464-(chloromethyl)-7-hydroxy-2H-chromen-2-oneYield 97.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
60 °C

Procedure

Resorcinol (275 g) was dissolved in acetic acid (560 mL) at 50° C. to prepare a solution. Separately, ethyl 4-chloroacetoacetate (205 g) was dissolved in acetic acid (187 ml), and concentrated sulfuric acid (100 mL) was added at 8° C. The solution was added at 8° C. to the resorcinol solution prepared in advance, and the mixture was stirred at 25° C. for 1 hr and at 60° C. for 3 hr. Warm water (3.24 L) was added at 40° C., and the mixture was stirred at 25° C. for 2 hr. The precipitated solid was collected by filtration. The solid was washed with water and air-dried to give the title compound (255 g) as a yellow solid.

Workup

  1. customto prepare a solution
  2. customprepared in advance
  3. stirringthe mixture was stirred at 25° C. for 2 hr
  4. filtrationThe precipitated solid was collected by filtration
  5. washThe solid was washed with water
  6. customair-dried

Sources & evidence

ORD record
ord-18cdc243ca7142598d9b98dddac4a1a3
Source dataset
uspto-grants-2015_02
Patent number
US08952185B2

Reaction notes

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