Water → 4-(chloromethyl)-7-hydroxy-8-methyl-2H-chromen-2-one

HRID 1020924Notes

Reaction equation

HRID 1020924 reaction equation
[CH3:1][C:2]1[C:8]([OH:9])=[CH:7][CH:6]=[CH:5][C:3]=1[OH:4].[Cl:10][CH2:11][C:12](=O)[CH2:13][C:14](OCC)=[O:15].O>CS(O)(=O)=O>[Cl:10][CH2:11][C:12]1[C:5]2[C:3](=[C:2]([CH3:1])[C:8]([OH:9])=[CH:7][CH:6]=2)[O:4][C:14](=[O:15])[CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 118432-MethylresorcinolHCID 69484Ethyl 4-chloroacetoacetate

Product 1

HCID 54238774-(chloromethyl)-7-hydroxy-8-methyl-2H-chromen-2-oneYield 90%

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Procedure

A solution of 2-methylresorcinol (1 g) in 10 mL of methyl sulfonic acid is introduced into a flask and then 1.3 equivalents (1.42 ml) of ethyl 4-chloroacetoacetate are added dropwise. After 1 night of stirring at room temperature, the mixture is cooled to 0° C. and then 50 mL of water are added. The residue is then filtered, dried and washed with diethyl ether in order to obtain 1.63 g (90%) of the compound 5.

Workup

  1. temperaturethe mixture is cooled to 0° C.
  2. filtrationThe residue is then filtered
  3. customdried
  4. washwashed with diethyl ether in order

Sources & evidence

ORD record
ord-b054d0cf8b9046979387158681a16dff
Source dataset
uspto-grants-2014_05
Patent number
US08716496B2

Reaction notes

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