Water → HCID 19972708, compound

HRID 2259880Notes

Reaction equation

HRID 2259880 reaction equation
[O:1]1[CH2:5][CH:2]1[CH2:3]Cl.[OH:6][C:7]1[C:16]2[O:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:13]([CH3:23])[C:12](=[O:24])[C:11]=2[CH:10]=[CH:9][CH:8]=1.[OH-].[Na+].O>C(O)C>[O:1]1[CH2:5][CH:2]1[CH2:3][O:6][C:7]1[C:16]2[O:15][C:14]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[C:13]([CH3:23])[C:12](=[O:24])[C:11]=2[CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 19972623HCID 19972623, compound

Product 1

HCID 19972708HCID 19972708, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

7 ml of 2,3-epoxypropyl chloride was added dropwise at 20-25° C. to a stirred mixture of 5 g of 8-hydroxy-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran and 9.7 ml of 2N aqueous sodium hydroxide solution in 10 ml of ethanol. After 6 hours at 20°-25° C., the reaction mixture was poured into 100 ml of water and the precipitate which formed was collected by suction filtration. After drying and purifying by flash chromatography on silica gel (eluant petroleum ether: ethyl acetate (65:35), there was obtained 4.45 g of the title compound, m.p. 128°-129° C.

Workup

  1. customthe precipitate which formed
  2. filtrationwas collected by suction filtration
  3. customAfter drying
  4. custompurifying by flash chromatography on silica gel (eluant petroleum ether: ethyl acetate (65:35)

Sources & evidence

ORD record
ord-db24c3e4384343fbb5348ef7a2b6dec0
Source dataset
uspto-grants-1995_12
Patent number
US05474994

Reaction notes

Loading…