Water → HCID 19972646, compound

HRID 2259859Notes

Reaction equation

HRID 2259859 reaction equation
[OH:1][C:2]1[C:11]2[O:10][C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:8]([CH3:18])[C:7](=[O:19])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:20](=O)([O-])[O-].[K+].[K+].O.Cl[CH2:28][Cl:29]>CN(C)C=O>[Cl:29][CH2:28][CH2:20][O:1][C:2]1[C:11]2[O:10][C:9]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[C:8]([CH3:18])[C:7](=[O:19])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 19972623HCID 19972623, compound

Product 1

HCID 19972646HCID 19972646, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 7.52 g of 8-hydroxy-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran (prepared as described in Da Re, P. et al., Ann. Chim., 1962, p. 506 et seq.), 6.22 g of anhydrous potassium carbonate and 25.5 ml of 1-bromo-2-chloromethane in 70 ml of dimethylformamide was stirred at 60° C. for 25 hours. The mixture was cooled to 20°-25° C. and poured into 600 ml of water. The organic solution, obtained by extraction with dichloromethane, was washed with aqueous sodium chloride solution and dried on anhydrous sodium sulfate. The solvents and excess 1-bromo-2-chloromethane were evaporated off in vacuo to yield 8.8 g of the title compound, m.p. 141°-142° C. after crystallization from chloroform:hexane.

Workup

  1. temperatureThe mixture was cooled to 20°-25° C.
  2. washwas washed with aqueous sodium chloride solution
  3. dry with materialdried on anhydrous sodium sulfate
  4. customThe solvents and excess 1-bromo-2-chloromethane were evaporated off in vacuo

Sources & evidence

ORD record
ord-a6183b05658a4242a349b2f9c6e7b003
Source dataset
uspto-grants-1995_12
Patent number
US05474994

Reaction notes

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